Chiral Phosphoric Acids as Versatile Catalysts for Enantioselective Transformations

Abstract

Chiral phosphoric acids derived from axially chiral biaryls and related chiral Brønsted acids have emerged as an attractive and widely applicable class of enantioselective organocatalysts for a variety of organic transformations. This review focuses on recent achievements in the development of enantioselective transformations using these axially chiral phosphoric acids and their analogues as chiral Brønsted acid catalysts. The contents are arranged according to the specific types of carbon-carbon bond-forming reactions, followed by carbon-heteroatom bond-forming reactions and functional group transformations, including reduction and oxidation. Further applications to combined phosphoric acid and metal complex catalytic systems and new aspects in the development of chiral Brønsted acid catalysts are also highlighted.

1 Introduction

2 Chiral Phosphoric Acids as Enantioselective Brønsted Acid Catalysts

3 Mannich and Related Reactions

4 One-Carbon Homologation Reactions via Activation of Imines

5 Friedel-Crafts and Related Reactions

6 Ene (Type) Reactions

7 Cycloaddition Reactions

8 Cyclization Reactions

9 Transformations via Protonation of Electron-Rich Double Bonds

10 Miscellaneous Carbon-Carbon Bond-Forming Reactions

11 Carbon-Heteroatom Bond-Forming Reactions

12 Transfer Hydrogenation Reactions

13 Oxidations

14 Combined Use of Metal Complex and Phosphoric Acid Catalysts

15 New Aspects in the Development of Chiral Brønsted Acid Catalysts

16 Conclusions

asymmetric catalysis - diastereoselectivity - electrophilic addition - enantioselectivity - multicomponent reaction

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For a review, see:

<A NAME="RE26710SS-87A">87a</A> Matsubara R. Kobayashi S. Acc. Chem. Res.  2008,  41:  292 

For aza-ene type reactions of α-imino esters, see:

<A NAME="RE26710SS-87B">87b</A> Matsubara R. Nakamura Y. Kobayashi S. Angew. Chem. Int. Ed.  2004,  43:  1679 

<A NAME="RE26710SS-87C">87c</A> Kiyohara H. Matsubara R. Kobayashi S. Org. Lett.  2006,  8:  5333 

For aza-ene type reactions of glyoxylates, see:

<A NAME="RE26710SS-87D">87d</A> Matsubara R. Nakamura Y. Kobayashi S. Angew. Chem. Int. Ed.  2004,  43:  3258 

<A NAME="RE26710SS-87E">87e</A> Matsubara R. Vital P. Nakamura Y. Kiyohara H. Kobayashi S. Tetrahedron  2004,  60:  9769 

<A NAME="RE26710SS-87F">87f</A> Matsubara R. Kawai N. Kobayashi S. Angew. Chem. Int. Ed.  2006,  45:  3814 

<A NAME="RE26710SS-87G">87g</A> Matsubara R. Doko T. Uetake R. Kobayashi S. Angew. Chem. Int. Ed.  2007,  46:  3047 

For some excellent studies of low loading of organocatalyst (less than 0.5 mol%), see:

<A NAME="RE26710SS-88A">88a</A> Su JT. Vachal P. Jacobsen EN. Adv. Synth. Catal.  2001,  343:  197 

<A NAME="RE26710SS-88B">88b</A> Saaby S. Bella M. Jørgensen AK. J. Am. Chem. Soc.  2004,  126:  8120 

<A NAME="RE26710SS-88C">88c</A> Shirakawa S. Yamamoto K. Kitamura M. Ooi T. Maruoka K. Angew. Chem. Int. Ed.  2005,  44:  625 

<A NAME="RE26710SS-88D">88d</A> Kitamura M. Shirakawa S. Maruoka K. Angew. Chem. Int. Ed.  2005,  44:  1549 

<A NAME="RE26710SS-88E">88e</A> Terada M. Ube H. Yaguchi Y. J. Am. Chem. Soc.  2006,  128:  1454 

<A NAME="RE26710SS-88F">88f</A> Terada M. Nakano M. Ube H. J. Am. Chem. Soc.  2006,  128:  16044 

<A NAME="RE26710SS-88G">88g</A> Rueping M. Antonchick AP. Theissmann T. Angew. Chem. Int. Ed.  2006,  45:  6751 

<A NAME="RE26710SS-88H">88h</A> Guo Q.-S. Du D.-M. Xu J. Angew. Chem. Int. Ed.  2008,  47:  759 

<A NAME="RE26710SS-88I">88i</A> Cheon CH. Yamamoto H. J. Am. Chem. Soc.  2008,  130:  9246 

<A NAME="RE26710SS-88J">88j</A> Liu X. Sun B. Deng L. Synlett  2009,  1685 

<A NAME="RE26710SS-89">89</A> Terada M. Machioka K. Sorimachi K. Angew. Chem. Int. Ed.  2006,  45:  2254 

For recent reviews, see:

<A NAME="RE26710SS-90A">90a</A> Enders D. Grondal C. Hüttl MRM. Angew. Chem. Int. Ed.  2007,  46:  1570 

<A NAME="RE26710SS-90B">90b</A> Yu X. Wang W. Org. Biomol. Chem.  2008,  6:  2037 

<A NAME="RE26710SS-91">91</A> Terada M. Machioka K. Sorimachi K. J. Am. Chem. Soc.  2007,  129:  10336 

For recent selected examples, see:

<A NAME="RE26710SS-92A">92a</A> Denmark SE. Bui T. J. Org. Chem.  2005,  70:  10190 

<A NAME="RE26710SS-92B">92b</A> Boxer MB. Yamamoto H. Nature Protocols  2006,  1:  2434 

<A NAME="RE26710SS-92C">92c</A> Boxer MB. Yamamoto H. J. Am. Chem. Soc.  2006,  128:  48 

<A NAME="RE26710SS-92D">92d</A> Boxer MB. Yamamoto H. J. Am. Chem. Soc.  2007,  129:  2762 

<A NAME="RE26710SS-92E">92e</A> Hayashi Y. Itoh T. Aratake S. Ishikawa H. Angew. Chem. Int. Ed.  2008,  47:  2082 

<A NAME="RE26710SS-92F">92f</A> Yang JW. Chandler C. Stadler M. Kampen D. List B. Nature  2008,  452:  453 

<A NAME="RE26710SS-92G">92g</A> Hayashi Y. Itoh T. Ohkubo M. Ishikawa H. Angew. Chem. Int. Ed.  2008,  47:  4722 

<A NAME="RE26710SS-93A">93a</A> Gaulon C. Gizecki P. Dhal R. Dujardin G. Synlett  2002,  952 

<A NAME="RE26710SS-93B">93b</A> Prashad M. Lu Y. Repič O. J. Org. Chem.  2004,  69:  584 

<A NAME="RE26710SS-94">94</A> Terada M. Machioka K. Sorimachi K. Angew. Chem. Int. Ed.  2009,  48:  2553 

<A NAME="RE26710SS-95">95</A> Dagousset G. Drouet F. Masson G. Zhu J. Org. Lett.  2009,  11:  5546 

<A NAME="RE26710SS-96">96</A> Liu H. Dagousset G. Masson G. Retailleau P. Zhu J.
J. Am. Chem. Soc.  2009,  131:  4598 

<A NAME="RE26710SS-97">97</A> Terada M. Soga K. Momiyama N. Angew. Chem. Int. Ed.  2008,  47:  4122 

<A NAME="RE26710SS-98">98</A> Terada M. Ikehara T. Ube H. J. Am. Chem. Soc.  2007,  129:  14112 ; and references cited therein

For X-ray crystal structure analysis of the double hydrogen bonding interaction between carboxylic acid and dimethylformamide, see:

<A NAME="RE26710SS-99A">99a</A> Czugler M. Stezowski JJ. Weber E. J. Chem. Soc., Chem. Commun.  1983,  154 

<A NAME="RE26710SS-99B">99b</A> Csöregh I. Sjögren A. Czugler M. Cserzö M. Weber E. J. Chem. Soc., Perkin Trans. 2  1986,  507 

<A NAME="RE26710SS-100">100</A> For hydrogen bonding in complexes of Lewis acids with formyl C-H hydrogen, see: Corey EJ. Lee T. Chem. Commun.  2001,  1321 

For reviews, see:

<A NAME="RE26710SS-101A">101a</A> Snider BB. In Comprehensive Organic Synthesis   Vol. 2:  Trost BM. Fleming I. Pergamon Press; Oxford: 1991.  p.527 

<A NAME="RE26710SS-101B">101b</A> Mikami K. Shimizu M. Chem. Rev.  1992,  92:  1021 

<A NAME="RE26710SS-101C">101c</A> Clarke M. France MB. Tetrahedron  2008,  64:  9003 

<A NAME="RE26710SS-102A">102a</A> Mikami K. Terada M. Narisawa S. Nakai T. Synlett  1992,  255 

<A NAME="RE26710SS-102B">102b</A> Berrisford DJ. Bolm C. Angew. Chem. Int. Ed.  1995,  34:  1717 

<A NAME="RE26710SS-102C">102c</A> Mikami K. Terada M. In Comprehensive Asymmetric Catalysis   Vol. 3:  Jacobsen EN. Pfaltz A. Yamamoto H. Springer; Berlin: 1999.  p.1143 

<A NAME="RE26710SS-103">103</A> Clarke MW. Jones CES. France MB. Beilstein J. Org. Chem.  2007,  3:  24 

<A NAME="RE26710SS-104">104</A> Rueping M. Theissmann T. Kuenkel A. Koenigs RM. Angew. Chem. Int. Ed.  2008,  47:  6798 

<A NAME="RE26710SS-105">105</A> Akiyama T. Tamura Y. Itoh J. Morita H. Fuchibe K. Synlett  2006,  141 

<A NAME="RE26710SS-106">106</A> Itoh J. Fuchibe K. Akiyama T. Angew. Chem. Int. Ed.  2006,  45:  4796 

<A NAME="RE26710SS-107">107</A> Liu H. Cun L.-F. Mi A.-Q. Jiang Y.-Z. Gong L.-Z. Org. Lett.  2006,  8:  6023 

<A NAME="RE26710SS-108">108</A> Rueping M. Azap C. Angew. Chem. Int. Ed.  2006,  45:  7832 

<A NAME="RE26710SS-109">109</A> Akiyama T. Morita H. Fuchibe K. J. Am. Chem. Soc.  2006,  128:  13070 

<A NAME="RE26710SS-110">110</A> Bergonzini G. Gramigna L. Mazzanti A. Fochi M. Bernardi L. Ricci A. Chem. Commun.  2010,  46:  327 

For reviews, see:

<A NAME="RE26710SS-111A">111a</A> Narasaka K. Synthesis  1991,  1 

<A NAME="RE26710SS-111B">111b</A> Kagan HB. Riant O. Chem. Rev.  1992,  92:  1007 

<A NAME="RE26710SS-111C">111c</A> Evans DA. Johnson JS. In Comprehensive Asymmetric Catalysis   Vol. 3:  Jacobsen EN. Pfaltz A. Yamamoto H. Springer Verlag; Berlin: 1999.  p.1177 

<A NAME="RE26710SS-111D">111d</A> Hayashi Y. In Cycloaddition Reactions in Organic Synthesis   Kobayashi S. Jørgensen KA. Wiley-VCH; Weinheim: 2002.  p.5 

<A NAME="RE26710SS-111E">111e</A> Corey EJ. Angew. Chem. Int. Ed.  2002,  41:  1650 

<A NAME="RE26710SS-112">112</A> For a recent review, see: Merino P. Marqués-López E. Tejero T. Herrera RP. Synthesis  2010,  1 

<A NAME="RE26710SS-113">113</A> Yagupolskii LM. Petric VN. Kondratenko NV. Sooväli L. Kaljurand I. Leito I. Koppel IA. J. Chem. Soc., Perkin Trans. 2  2002,  1950 

<A NAME="RE26710SS-114A">114a</A> Ooi T. Maruoka K. In Comprehensive Asymmetric Catalysis   Vol. 3:  Jacobsen EN. Pfaltz A. Yamamoto H. Springer-Verlag; Berlin: 1999.  p.1237 

<A NAME="RE26710SS-114B">114b</A> Jørgensen KA. In Cycloaddition Reactions in Organic Synthesis   Kobayashi S. Jørgensen KA. Wiley-VCH; Weinheim: 2002.  p.151 

For representative recent reviews of asymmetric hetero-Diels-Alder reactions, see:

<A NAME="RE26710SS-115A">115a</A> Jørgensen KA. Angew. Chem. Int. Ed.  2000,  39:  3558 

<A NAME="RE26710SS-115B">115b</A> Jørgensen KA. Eur. J. Org. Chem.  2004,  2093 

<A NAME="RE26710SS-115C">115c</A> Lin L. Liu X. Feng X. Synlett  2007,  2147 

<A NAME="RE26710SS-115D">115d</A> Pellisser H. Tetrahedron  2009,  65:  2839 

For representative examples of catalytic enantioselective hetero-Diels-Alder reactions of aldehydes with siloxy- or methoxydienes, see:

<A NAME="RE26710SS-116A">116a</A> Mikami K. Motoyama Y. Terada M. J. Am. Chem. Soc.  1994,  116:  2812 

<A NAME="RE26710SS-116B">116b</A> Dossetter AG. Jamison TF. Jacobsen EN. Angew. Chem. Int. Ed.  1999,  38:  2398 

<A NAME="RE26710SS-116C">116c</A> Quitschalle M. Christmann M. Bhatt U. Kalesse M. Tetrahedron Lett.  2001,  42:  1263 

<A NAME="RE26710SS-117A">117a</A> Danishefsky SJ. Larson E. Askin D. Kato N. J. Am. Chem. Soc.  1985,  107:  1246 

<A NAME="RE26710SS-117B">117b</A> Jurczak J. Golebiowski A. Rahm A. Tetrahedron Lett.  1986,  27:  853 

<A NAME="RE26710SS-117C">117c</A> McCarrick MA. Wu YD. Houk KN. J. Org. Chem.  1993,  58:  3330 

<A NAME="RE26710SS-117D">117d</A> Zhang X. Du H. Wang Z. Wu YD. Ding K. J. Org. Chem.  2006,  71:  2862 

<A NAME="RE26710SS-118">118</A> Only one example of the catalytic asymmetric anti-selective hetero-Diels-Alder reaction has been reported using Danishefsky’s dienes. See: Yamashita Y. Saito S. Ishitani H. Kobayashi S. J. Am. Chem. Soc.  2003,  125:  3793 

<A NAME="RE26710SS-119">119</A> Momiyama N. Tabuse H. Terada M. J. Am. Chem. Soc.  2009,  131:  12882 

<A NAME="RE26710SS-120">120</A>

The double hydrogen bonding model of the TS structure has been proposed in the aza-ene type reaction of glyoxylate 124 with enecarbamate 105, see ref. 97.

For reviews, see:

<A NAME="RE26710SS-121A">121a</A> Gothelf KV. Jørgensen KA. Chem. Commun.  2000,  1449 

<A NAME="RE26710SS-121B">121b</A> Kanemasa S. Synlett  2002,  1371 

<A NAME="RE26710SS-121C">121c</A> Nair V. Suja TD. Tetrahedron  2007,  63:  12247 

<A NAME="RE26710SS-122">122</A> Jiao P. Nakashima D. Yamamoto H. Angew. Chem. Int. Ed.  2008,  47:  2411 

<A NAME="RE26710SS-123">123</A> For an example, see: Simonsen KB. Bayón P. Hazell RG. Gothelf KV. Jørgensen KA. J. Am. Chem. Soc.  1999,  121:  3845 

For reviews, see:

<A NAME="RE26710SS-124A">124a</A> Gothelf KV. Jørgensen KA. Chem. Rev.  1998,  98:  863 

<A NAME="RE26710SS-124B">124b</A> Nájera C. Sansano JM. Angew. Chem. Int. Ed.  2005,  44:  6272 

<A NAME="RE26710SS-124C">124c</A> Husinec S. Savic V. Tetrahedron: Asymmetry  2005,  16:  2047 

<A NAME="RE26710SS-124D">124d</A> Pandey G. Banerjee P. Gadre SR. Chem. Rev.  2006,  106:  4484 

<A NAME="RE26710SS-124E">124e</A> Bonin M. Chauveau A. Micouin L. Synlett  2006,  2349 

<A NAME="RE26710SS-124F">124f</A> Pellisier H. Tetrahedron  2007,  63:  3235 

<A NAME="RE26710SS-124G">124g</A> Stanley LM. Sibi MP. Chem. Rev.  2008,  108:  2887 

<A NAME="RE26710SS-125">125</A> Chen X.-H. Zhang W.-Q. Gong L.-Z. J. Am. Chem. Soc.  2008,  130:  5652 

<A NAME="RE26710SS-126">126</A> Liu W.-J. Chen X.-H. Gong L.-Z. Org. Lett.  2008,  10:  5357 

<A NAME="RE26710SS-127">127</A> Yu J. Chen X.-H. Song J. Chen W.-J. Gong L.-Z. Org. Lett.  2009,  11:  4946 

<A NAME="RE26710SS-128">128</A> Chen X.-H. Wei Q. Luo S.-W. Xiao H. Gong L.-Z.
J. Am. Chem. Soc.  2009,  131:  13819 

<A NAME="RE26710SS-129A">129a</A> Denmark SE. In Comprehensive Organic Synthesis   Vol. 5:  Trost BM. Fleming I. Pergamon Press; Oxford: 1991.  p.51 

<A NAME="RE26710SS-129B">129b</A> Habermas KL. Denmark SE. Jones TK. Org. React.  1994,  45:  1 

<A NAME="RE26710SS-129C">129c</A> Pellissier H. Tetrahedron  2005,  61:  6479 

<A NAME="RE26710SS-129D">129d</A> Frontier AJ. Collison C. Tetrahedron  2005,  61:  7577 

<A NAME="RE26710SS-129E">129e</A> Tius MA. Eur. J. Org. Chem.  2005,  2193 

<A NAME="RE26710SS-130A">130a</A> Liang G. Gradl SN. Trauner D. Org. Lett.  2003,  5:  4931 

<A NAME="RE26710SS-130B">130b</A> Aggarwal VK. Belfield AJ. Org. Lett.  2003,  5:  5075 

<A NAME="RE26710SS-130C">130c</A> Liang G. Trauner D. J. Am. Chem. Soc.  2004,  126:  9544 

<A NAME="RE26710SS-130D">130d</A> Walz I. Togni A. Chem. Commun.  2008,  4315 

<A NAME="RE26710SS-130E">130e</A> Yaji K. Shindo M. Synlett  2009,  2524 

<A NAME="RE26710SS-131">131</A> Rueping M. Ieawsuwan W. Antonchick AP. Nachtsheim BJ. Angew. Chem. Int. Ed.  2007,  46:  2097 

<A NAME="RE26710SS-132">132</A> Rueping M. Ieawsuwan W. Adv. Synth. Catal.  2009,  351:  78 

<A NAME="RE26710SS-133">133</A> Muller S. List B. Angew. Chem. Int. Ed.  2009,  48:  9975 

<A NAME="RE26710SS-134">134</A> For the chiral phosphoric acid catalyzed consecutive condensation/6π-electrocyclization of 4-hydroxycoumarin with crotonaldehyde to give a chromenone derivative with low enantioselectivity, see: Moreau J. Hubert C. Batany J. Toupet L. Roisnel T. Hurvois J.-P. Renaud J.-L.
J. Org. Chem.  2009,  74:  8963 

For selected reviews, see:

<A NAME="RE26710SS-135A">135a</A> Burke MD. Schreiber SL. Angew. Chem. Int. Ed.  2004,  43:  46 

<A NAME="RE26710SS-135B">135b</A> Multicomponent Reactions   Zhu J. Bienaymé H. Wiley-VCH; Weinheim: 2005. 

<A NAME="RE26710SS-135C">135c</A> Ramon DJ. Yus M. Angew. Chem. Int. Ed.  2005,  44:  1602 

<A NAME="RE26710SS-135D">135d</A> Guillena G. Ramon DJ. Yus M. Tetrahedron: Asymmetry  2007,  18:  693 

<A NAME="RE26710SS-135E">135e</A> Toure BB. Hall DG. Chem. Rev.  2009,  109:  4439 

<A NAME="RE26710SS-136A">136a</A> Jiang J. Yu J. Sun X.-X. Rao Q.-Q. Gong L.-Z. Angew. Chem. Int. Ed.  2008,  47:  2458 

See also:

<A NAME="RE26710SS-136B">136b</A> Moreau J. Duboc A. Hubert C. Hurvois J.-P. Renaud J.-L. Tetrahedron Lett.  2007,  48:  8647 

For reviews, see:

<A NAME="RE26710SS-137A">137a</A> Stout DM. Meyers AI. Chem. Rev.  1982,  82:  223 

<A NAME="RE26710SS-137B">137b</A> Lavilla R. J. Chem. Soc., Perkin Trans. 1  2002,  1411 

<A NAME="RE26710SS-138A">138a</A> Janis RA. Silver PJ. Triggle DJ. Adv. Drug Res.  1987,  16:  309 

<A NAME="RE26710SS-138B">138b</A> Bossert F. Vater W. Med. Res. Rev.  1989,  9:  291 

<A NAME="RE26710SS-139">139</A> Murakami Y. Kikuchi J.-i. Hisaeda Y. Chem. Rev.  1996,  96:  721 

<A NAME="RE26710SS-140">140</A> Evans CG. Gestwicki JE. Org. Lett.  2009,  11:  2957 

For reviews, see:

<A NAME="RE26710SS-141A">141a</A> Fisk JS. Mosey RA. Tepe JJ. Chem. Soc. Rev.  2007,  36:  1432 

<A NAME="RE26710SS-141B">141b</A> Hewlett NM. Hupp CD. Tepe JJ. Synthesis  2009,  2825 

<A NAME="RE26710SS-142">142</A> Jiang J. Qing J. Gong L.-Z. Chem. Eur. J.  2009,  15:  7031 

For proline-catalyzed reactions, see:

<A NAME="RE26710SS-143A">143a</A> Eder U. Sauer G. Wiechert R. Angew. Chem., Int. Ed. Engl.  1971,  10:  496 

<A NAME="RE26710SS-143B">143b</A> Hajos ZG. Parrish DR. J. Org. Chem.  1974,  39:  1615 

<A NAME="RE26710SS-143C">143c</A> Bui T. Barbas CF. Tetrahedron Lett.  2000,  41:  6951 

<A NAME="RE26710SS-143D">143d</A> Cheong PH.-Y. Houk KN. Warrier JS. Hanessian S. Adv. Synth. Catal.  2004,  346:  1111 

<A NAME="RE26710SS-143E">143e</A> Inomata K. Barragué M. Paquette LA. J. Org. Chem.  2005,  70:  533 

<A NAME="RE26710SS-143F">143f</A> Clemente FR. Houk KN. J. Am. Chem. Soc.  2005,  127:  11294 

<A NAME="RE26710SS-143G">143g</A> Lacoste E. Vaique E. Berlande M. Pianet I. Vincent J.-M. Landais Y. Eur. J. Org. Chem.  2007,  167 

<A NAME="RE26710SS-144">144</A> Akiyama T. Katoh T. Mori K. Angew. Chem. Int. Ed.  2009,  48:  4226 

<A NAME="RE26710SS-145">145</A> Mori K. Katoh T. Suzuki T. Noji T. Yamanaka M. Akiyama T. Angew. Chem. Int. Ed.  2009,  48:  9652 

<A NAME="RE26710SS-146">146</A> Terada M. Sorimachi K. J. Am. Chem. Soc.  2007,  129:  292 

<A NAME="RE26710SS-147A">147a</A> Terada M. Tanaka H. Sorimachi K. Synlett  2008,  1661 

See also:

<A NAME="RE26710SS-147B">147b</A> Kobayashi S. Gustafsson T. Shimizu Y. Kiyohara H. Matsubara R. Org. Lett.  2006,  6:  4923 

<A NAME="RE26710SS-148">148</A> Jia Y.-X. Zhong J. Zhu S.-F. Zhang C.-M. Zhou Q.-L. Angew. Chem. Int. Ed.  2007,  46:  5565 

<A NAME="RE26710SS-149">149</A> Baudequin C. Zamfir A. Tsogoeva SB. Chem. Commun.  2008,  4637 

<A NAME="RE26710SS-150">150</A> For a review of enantioselective protonation, see: Duhamel L. Duhamel P. Plaquevent JC. Tetrahedron: Asymmetry  2004,  15:  3635 

<A NAME="RE26710SS-151">151</A> For the development of BINOL-derived phosphorodithioic acids, see: Pousse G. Devineau A. Dalla V. Humphreys L. Lasne M.-C. Rouden J. Blanchet J. Tetrahedron  2009,  65:  10617 

<A NAME="RE26710SS-152">152</A> Mayer S. List B. Angew. Chem. Int. Ed.  2006,  45:  4193 ; and references cited therein

<A NAME="RE26710SS-153">153</A> Terada M. Tanaka H. Sorimachi K. J. Am. Chem. Soc.  2009,  131:  3430 

<A NAME="RE26710SS-154">154</A> Reisman SE. Doyle AG. Jacobsen EN. J. Am. Chem. Soc.  2008,  130:  7198 

For reviews on the semi-pinacol rearrangement, see:

<A NAME="RE26710SS-155A">155a</A> Rickborn B. In Comprehensive Organic Synthesis   Vol. 3:  Trost BM. Fleming I. Pergamon Press; Oxford: 1991.  p.733 

<A NAME="RE26710SS-155B">155b</A> Snape T. Chem. Soc. Rev.  2007,  36:  1823 

<A NAME="RE26710SS-156">156</A> Zhang Q.-W. Fan C.-A. Zhang H.-J. Tu Y.-Q. Zhao Y.-M. Gu P. Chen Z.-M. Angew. Chem. Int. Ed.  2009,  48:  8572 

For recent reviews, see:

<A NAME="RE26710SS-157A">157a</A> Widenhoefer RA. Chem. Eur. J.  2008,  14:  5382 

<A NAME="RE26710SS-157B">157b</A> Mueller TE. Hultzsch KC. Yus M. Foubelo F. Tada M. Chem. Rev.  2008,  108:  3795 

<A NAME="RE26710SS-157C">157c</A> Severin R. Doye S. Chem. Soc. Rev.  2007,  36:  1407 

<A NAME="RE26710SS-157D">157d</A> Aillaud I. Collin J. Hannedouche J. Schulz E. Dalton Trans.  2007,  5105 

<A NAME="RE26710SS-158">158</A> Ackermann L. Althammer A. Synlett  2008,  995 

For reviews, see:

<A NAME="RE26710SS-159A">159a</A> The Claisen Rearrangement   Hiersemann M. Nubbemeyer U. Wiley-VCH; Weinheim: 2007. 

<A NAME="RE26710SS-159B">159b</A> Martin Castro AM. Chem. Rev.  2004,  104:  2939 

<A NAME="RE26710SS-160">160</A> Rueping M. Antonchick AP. Angew. Chem. Int. Ed.  2008,  47:  10090 

For reviews, see:

<A NAME="RE26710SS-161A">161a</A> Radicals in Organic Synthesis   Vols. 1 and 2:  Renaud P. Sibi MP. Wiley-VCH; Weinheim: 2001. 

<A NAME="RE26710SS-161B">161b</A> Sibi MP. Manyem S. Zimmerman J. Chem. Rev.  2003,  103:  3263 

<A NAME="RE26710SS-161C">161c</A> Bar G. Parsons AF. Chem. Soc. Rev.  2003,  32:  251 

<A NAME="RE26710SS-161D">161d</A> Zimmerman J. Sibi MP. Top. Curr. Chem.  2006,  263:  107 

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<A NAME="RE26710SS-163B">163b</A> Cozzi PG. Benfatti F. Zoli L. Angew. Chem. Int. Ed.  2009,  48:  1313 

See also:

<A NAME="RE26710SS-163C">163c</A> Melchiorre P. Angew. Chem. Int. Ed.  2009,  48:  1360 

<A NAME="RE26710SS-164">164</A> Guo Q.-X. Peng Y.-G. Zhang J.-W. Song L. Feng Z. Gong L.-Z. Org. Lett.  2009,  11:  4620 

<A NAME="RE26710SS-165">165</A> For a review of enantioselective synthesis of α-amino phosphonate derivatives, see: Ma J.-A. Chem. Soc. Rev.  2006,  35:  630 

<A NAME="RE26710SS-166">166</A> Akiyama T. Morita H. Itoh J. Fuchibe K. Org. Lett.  2005,  7:  2583 

For computational analysis of transition states, see:

<A NAME="RE26710SS-167A">167a</A> Akiyama T. Morita H. Bachu P. Mori K. Yamanaka M. Hirata T. Tetrahedron  2009,  65:  4950 

<A NAME="RE26710SS-167B">167b</A> Yamanaka M. Hirata T. J. Org. Chem.  2009,  74:  3266 

<A NAME="RE26710SS-168">168</A> Cheng X. Goddard R. Buth G. List B. Angew. Chem. Int. Ed.  2008,  47:  5079 

<A NAME="RE26710SS-169">169</A> Hoffmann S. Nicoletti M. List B. J. Am. Chem. Soc.  2006,  128:  13074 

<A NAME="RE26710SS-170">170</A> Rowland GB. Zhang H. Rowland EB. Chennamadhavuni S. Wang Y. Antilla JC. J. Am. Chem. Soc.  2005,  127:  15696 

<A NAME="RE26710SS-171">171</A> Liang Y. Rowland EB. Rowland GB. Perman JA. Antilla JC. Chem. Commun.  2007,  4477 

<A NAME="RE26710SS-172">172</A> Cheng X. Vellalath S. Goddard R. List B. J. Am. Chem. Soc.  2008,  130:  15786 

<A NAME="RE26710SS-173">173</A> Rueping M. Antonchick AP. Sugiono E. Grenader K. Angew. Chem. Int. Ed.  2009,  48:  908 

<A NAME="RE26710SS-174">174</A> Li G. Fronczek FR. Antilla JC. J. Am. Chem. Soc.  2008,  130:  12216 

<A NAME="RE26710SS-175">175</A> For a review, see: Yudin AK. Aziridines and Epoxides in Organic Synthesis   Wiley-VCH; Weinheim: 2006. 

<A NAME="RE26710SS-176">176</A> For a review, see: Schneider C. Angew. Chem. Int. Ed.  2009,  48:  2082 

<A NAME="RE26710SS-177">177</A> Rowland EB. Rowland GB. Rivera-Otero E. Antilla JC. J. Am. Chem. Soc.  2007,  129:  12084 

<A NAME="RE26710SS-178">178</A> Larson SE. Baso JC. Li G. Antilla JC. Org. Lett.  2009,  11:  5186 

<A NAME="RE26710SS-179">179</A> Della Sala G. Lattanzi A. Org. Lett.  2009,  11:  3330 

<A NAME="RE26710SS-180A">180a</A> Hamilton GL. Kanai T. Toste FD. J. Am. Chem. Soc.  2008,  130:  14984 

For related chiral counteranion strategies for enantioselective transformations, see:

<A NAME="RE26710SS-180B">180b</A> Hamilton GL. Kang EJ. Mba M. Toste FD. Science  2007,  317:  496 

<A NAME="RE26710SS-180C">180c</A> LaLonde RL. Wang ZJ. Mba M. Lackner AD. Toste FD. Angew. Chem. Int. Ed.  2010,  49:  598 

For recent reviews, see:

<A NAME="RE26710SS-181A">181a</A> Ooi T. Maruoka K. Angew. Chem. Int. Ed.  2007,  46:  4222 

<A NAME="RE26710SS-181B">181b</A> Hashimoto T. Maruoka K. Chem. Rev.  2007,  107:  5656 

<A NAME="RE26710SS-181C">181c</A> Asymmetric Phase Transfer Catalysis   Maruoka K. Wiley-VCH; Weinheim: 2008. 

For reviews, see:

<A NAME="RE26710SS-182A">182a</A> Blaser H.-U. Malan C. Pugin B. Spindler F. Steiner H. Studer M. Adv. Synth. Catal.  2003,  345:  103 

<A NAME="RE26710SS-182B">182b</A> Tang W. Zhang X. Chem. Rev.  2003,  103:  3029 

<A NAME="RE26710SS-182C">182c</A> Riant O. Mostefaï N. Courmarcel J. Synthesis  2004,  2943 

<A NAME="RE26710SS-183A">183a</A> Yang JW. Hechavarria Foneca MT. Vignola N. List B. Angew. Chem. Int. Ed.  2005,  44:  110 

<A NAME="RE26710SS-183B">183b</A> Ouellet SG. Tuttle JB. MacMillan DWC. J. Am. Chem. Soc.  2005,  127:  32 

See also:

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For reviews, see:

<A NAME="RE26710SS-184A">184a</A> Ouellet SG. Walji AM. Macmillan DWC. Acc. Chem. Res.  2007,  40:  1327 

<A NAME="RE26710SS-184B">184b</A> You S.-L. Chem. Asian J.  2007,  2:  820 

<A NAME="RE26710SS-184C">184c</A> Connon SJ. Org. Biomol. Chem.  2007,  5:  3407 

<A NAME="RE26710SS-184D">184d</A> Rueping M. Sugiono E. Schoepke FR. Synlett  2010,  852 

<A NAME="RE26710SS-185">185</A> Rueping M. Sugiono E. Azap C. Theissmann T. Bolte M. Org. Lett.  2005,  7:  3781 

For theoretical studies, see:

<A NAME="RE26710SS-186A">186a</A> Simón L. Goodman JM. J. Am. Chem. Soc.  2008,  130:  8741 

<A NAME="RE26710SS-186B">186b</A> Marcelli T. Hammar P. Himo F. Chem. Eur. J.  2008,  14:  8562 

<A NAME="RE26710SS-187">187</A> Hoffmann S. Seayad AM. List B. Angew. Chem. Int. Ed.  2005,  44:  7424 

<A NAME="RE26710SS-188">188</A> Storer RI. Carrera DE. Ni Y. MacMillan DWC.
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<A NAME="RE26710SS-190">190</A> Li G. Liang Y. Antilla JC. J. Am. Chem. Soc.  2007,  129:  5830 

<A NAME="RE26710SS-191">191</A> Kang Q. Zhao Z.-A. You S.-L. Adv. Synth. Catal.  2007,  349:  1657 

<A NAME="RE26710SS-192">192</A> Kang Q. Zhao Z.-A. You S.-L. Org. Lett.  2008,  10:  2031 

<A NAME="RE26710SS-193">193</A> Li G. Antilla JC. Org. Lett.  2009,  11:  1075 

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<A NAME="RE26710SS-199">199</A> Rueping M. Antonchick AP. Angew. Chem. Int. Ed.  2007,  46:  4562 

<A NAME="RE26710SS-200">200</A> Metallinos C. Barrett FB. Xu S. Synlett  2008,  720 

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See also:

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For reviews, see:

<A NAME="RE26710SS-203A">203a</A> List B. Chem. Commun.  2006,  819 

<A NAME="RE26710SS-203B">203b</A> Palomo C. Mielgo A. Angew. Chem. Int. Ed.  2006,  45:  7876 

<A NAME="RE26710SS-203C">203c</A> Walji AM. MacMillan DWC. Synlett  2007,  1477 

<A NAME="RE26710SS-204">204</A> Zhou J. List B. J. Am. Chem. Soc.  2007,  129:  7498 

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<A NAME="RE26710SS-206">206</A> Rueping M. Antonchick AP. Angew. Chem. Int. Ed.  2008,  47:  5836 

For selected reviews on metal-catalyzed asymmetric epoxidations, see:

<A NAME="RE26710SS-207A">207a</A> Katsuki T. In Comprehensive Asymmetric Catalysis   Vol. 2:  Jacobsen EN. Pfaltz A. Yamamoto H. Springer-Verlag; Berlin: 1999.  p.621 

<A NAME="RE26710SS-207B">207b</A> Jacobsen EN. Wu MH. In Comprehensive Asymmetric Catalysis   Vol. 2:  Jacobsen EN. Pfaltz A. Yamamoto H. Springer-Verlag; Berlin: 1999.  p.649 

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<A NAME="RE26710SS-207D">207d</A> Xia Q.-H. Ge H.-Q. Ye C.-P. Liu Z.-M. Su K.-X. Chem. Rev.  2005,  105:  1603 

For selected reviews on organocatalytic asymmetric epoxidations, see:

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<A NAME="RE26710SS-208B">208b</A> Yang D. Acc. Chem. Res.  2004,  37:  497 

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<A NAME="RE26710SS-208F">208f</A> Berkessel A. Gröger H. Asymmetric Organocatalysis-From Biomimetic Concepts to Powerful Methods for Asymmetric Synthesis   Wiley-VCH; Weinheim: 2005.  p.277 

<A NAME="RE26710SS-209A">209a</A> Juliá S. Masana J. Vega JC. Angew. Chem., Int. Ed. Engl.  1980,  19:  929 

<A NAME="RE26710SS-209B">209b</A> Juliá S. Guixer J. Masana J. Rocas J. Colonna S. Annunziata R. Molinari H.
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<A NAME="RE26710SS-210">210</A> For a review on the asymmetric epoxidation of α,β-unsaturated carbonyl compounds, see: Porter MJ. Skidmore J. Chem. Commun.  2000,  1215 

<A NAME="RE26710SS-211">211</A> Wang X. List B. Angew. Chem. Int. Ed.  2008,  47:  1119 

<A NAME="RE26710SS-212">212</A> For a review, see: ten Brink G.-J. Arends IWCE. Sheldon RA. Chem. Rev.  2004,  104:  4105 

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<A NAME="RE26710SS-213B">213b</A> Xu S. Wang Z. Li Y. Zhang X. Wang H. Ding K. Chem. Eur. J.  2010,  16:  3021 

For Lewis acid catalyzed enantioselective α-hydroxylation of β-keto esters, see:

<A NAME="RE26710SS-214A">214a</A> Bonaccorsi C. Althaus M. Becker C. Togni A. Mezzetti A. Pure Appl. Chem.  2006,  78:  391 

<A NAME="RE26710SS-214B">214b</A> Ishimaru T. Shibata N. Nagai J. Nakamura S. Toru T. Kanemasa S. J. Am. Chem. Soc.  2006,  128:  16488 

For organocatalysis, see:

<A NAME="RE26710SS-214C">214c</A> Acocella MR. Mancheño OG. Bella M. Jørgensen KA. J. Org. Chem.  2004,  69:  8165 

<A NAME="RE26710SS-215">215</A> Lu M. Zhu D. Lu Y. Zeng X. Tan B. Xu Z. Zhong G. J. Am. Chem. Soc.  2009,  131:  4562 

For reviews, see:

<A NAME="RE26710SS-216A">216a</A> Merino P. Tejero T. Angew. Chem. Int. Ed.  2004,  43:  2995 

<A NAME="RE26710SS-216B">216b</A> Yamamoto H. Momiyama N. Chem. Commun.  2005,  3514 

For reviews, see:

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<A NAME="RE26710SS-217B">217b</A> Hashmi ASK. Hubbert C. Angew. Chem. Int. Ed.  2010,  49:  1010 

<A NAME="RE26710SS-217C">217c</A> de Armas P. Tejedor D. García-Tellado F. Angew. Chem. Int. Ed.  2010,  49:  1013 

<A NAME="RE26710SS-217D">217d</A> Zhou J. Chem. Asian J.  2010,  5:  422 

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<A NAME="RE26710SS-219A">219a</A> Kong J.-R. Ngai M.-Y. Krische MJ. J. Am. Chem. Soc.  2006,  128:  718 

<A NAME="RE26710SS-219B">219b</A> Ngai M.-Y. Kong J.-R. Krische MJ. J. Org. Chem.  2007,  72:  1063 

<A NAME="RE26710SS-220">220</A> Rueping M. Antonchick AP. Brinkmann C. Angew. Chem. Int. Ed.  2007,  46:  6903 

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<A NAME="RE26710SS-227B">227b</A> Trost BM. Jiang C. Synthesis  2006,  369 

<A NAME="RE26710SS-227C">227c</A> Cozzi PG. Hilgraf R. Zimmermann N. Eur. J. Org. Chem.  2007,  5969 

For a review of an organocatalytic approach, see:

<A NAME="RE26710SS-227D">227d</A> Bella M. Gasperi T. Synthesis  2009,  1583 

<A NAME="RE26710SS-228">228</A> Reetz MT. Westermann J. Kyung S.-H. Chem. Ber.  1985,  118:  1050 

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<A NAME="RE26710SS-230">230</A> Han Z.-Y. Xiao H. Chen X.-H. Gong L.-Z. J. Am. Chem. Soc.  2009,  131:  9182 

<A NAME="RE26710SS-231">231</A> Liu X.-Y. Che C.-M. Org. Lett.  2009,  11:  4204 

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<A NAME="RE26710SS-237B">237b</A> Hashimoto T. Maruoka K. Synthesis  2008,  3703 

<A NAME="RE26710SS-238">238</A> Hashimoto T. Uchiyama N. Maruoka K. J. Am. Chem. Soc.  2008,  130:  14380 

<A NAME="RE26710SS-239">239</A> Hashimoto T. Hirose M. Maruoka K. J. Am. Chem. Soc.  2008,  130:  7556 

<A NAME="RE26710SS-240">240</A> Hatano M. Maki T. Moriyama K. Arinobe M. Ishihara K. J. Am. Chem. Soc.  2008,  130:  16858 

List and co-workers employed 342a as a chiral Brønsted acid catalyst for the first time; however, no asymmetric induction was obtained. See:

<A NAME="RE26710SS-241A">241a</A> Pan SC. List B. Chem. Asian J.  2008,  3:  430 

<A NAME="RE26710SS-241B">241b</A> Kampen D. Ladépêche A. Claßen G. List B. Adv. Synth. Catal.  2008,  350:  962 

<A NAME="RE26710SS-242">242</A> García-García P. Lay F. García-García P. Rabalakos C. List B. Angew. Chem. Int. Ed.  2009,  48:  4363 

<A NAME="RE26710SS-243">243</A> Mathieu B. Ghosez L. Tetrahedron Lett.  1997,  38:  5497 

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<A NAME="RE26710SS-244D">244d</A> Akalay D. Dürner G. Bats JW. Bolte M. Göbel MW. J. Org. Chem.  2007,  72:  5618 

For an example of the stoichiometric use of a cationic chiral Brønsted acid, see:

<A NAME="RE26710SS-244E">244e</A> Jang DO. Kim SY. J. Am. Chem. Soc.  2008,  130:  16152 

<A NAME="RE26710SS-245A">245a</A> Uyeda C. Jacobsen EN. J. Am. Chem. Soc.  2008,  130:  9228 

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<A NAME="RE26710SS-247A">247a</A> Uraguchi D. Sakaki S. Ooi T. J. Am. Chem. Soc.  2007,  129:  12392 

<A NAME="RE26710SS-247B">247b</A> Uraguchi D. Ueki Y. Ooi T. J. Am. Chem. Soc.  2008,  130:  14088 

<A NAME="RE26710SS-247C">247c</A> Uraguchi D. Ito T. Ooi T. J. Am. Chem. Soc.  2009,  131:  3836 

<A NAME="RE26710SS-247D">247d</A> Uraguchi D. Ueki Y. Ooi T. Science  2009,  326:  120 

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