Enantioselective Phosphine
Organocatalysis

Angela Marinetti; Arnaud Voituriez

doi:10.1055/s-0029-1219157

ACCOUNT

Enantioselective Phosphine Organocatalysis

Angela Marinetti*, Arnaud Voituriez
Institut de Chimie des Substances Naturelles, CNRS UPR 2301, 1 avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France
Fax: +33(1)69077247; e-Mail: angela.marinetti@icsn.cnrs-gif.fr;

Abstract

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Abstract

The broad potential synthetic usefulness of phosphine-promoted reactions has stimulated many recent investigations on enantioselective variants of known reactions of this family, as well as the search for new, specifically designed, chiral phosphorus catalysts. This short overview summarizes the state of the art in this field and highlights the most significant achievements, with special emphasis on our recent work.

1 Introduction

2 Chiral Phosphine Organocatalysts

2.1 Cyclic and Bicyclic Phosphines

2.2 Acyclic Phosphines with Hydrogen-Bonding Functionalities

3 Enantioselective Phosphine-Promoted Reactions

3.1 Acylation of Alcohols and Other Acyl-Transfer Reactions

3.2 Morita-Baylis-Hillman-type Reactions

3.3 [3+2] and [4+2] Cyclizations between Allenes and Imines

3.4 [3+2] Cyclizations between Allenes and α,β-Unsaturated Ketones and Esters

3.5 Addition of Nucleophiles to Unsaturated Electron-Poor Substrates

3.6 Allylic Substitutions on Morita-Baylis-Hillman Adducts

3.7 Miscellaneous Reactions

4 Summary and Outlook

Key words

enantioselective catalysis - chiral phosphines - organocatalysis - nucleophilic activation

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Referenzen

References

<A NAME="RA54509ST-1A">1a</A> Lu X. Zhang C. Xu Z. Acc. Chem. Res. 2001, 34: 535

<A NAME="RA54509ST-1B">1b</A> Valentine DH. Hillhouse JH. Synthesis 2003, 317

<A NAME="RA54509ST-1C">1c</A> Methot JL. Roush WR. Adv. Synth. Catal. 2004, 346: 1035

<A NAME="RA54509ST-1D">1d</A> Ye L.-W. Zhou J. Tang Y. Chem. Soc. Rev. 2008, 37: 1140

<A NAME="RA54509ST-1E">1e</A> Methot JL. Roush WR. In Science of Synthesis Vol. 42: Mathey F. Thieme; Stuttgart: 2008. p.469-501

<A NAME="RA54509ST-1F">1f</A> Denmark SE. Beutner GL. Angew. Chem. Int. Ed. 2008, 47: 1560

<A NAME="RA54509ST-2">2</A> Börner A. Phosphorus Ligands in Asymmetric Catalysis Wiley-VCH; Weinheim: 2008.

<A NAME="RA54509ST-3A">3a</A> Trost BM. Kazmaier U. J. Am. Chem. Soc. 1992, 114: 7933

<A NAME="RA54509ST-3B">3b</A> Guo C. Lu X. J. Chem. Soc., Perkin Trans. 1 1993, 1921

<A NAME="RA54509ST-3C">3c</A> Kwong CK.-W. Fu MY. Lam CS.-L. Toy PH. Synthesis 2008, 2307

<A NAME="RA54509ST-4A">4a</A> Rauhut M, and Currier H. inventors; US Patent 3074999. (American Cyanamide Co.)

<A NAME="RA54509ST-4B">4b</A> Aroyan CE. Dermenci A. Miller SJ. Tetrahedron 2009, 65: 4069

<A NAME="RA54509ST-5A">5a</A> Morita K. Suzuki Z. Hirose H. Bull. Chem. Soc. Jpn. 1968, 41: 2815

<A NAME="RA54509ST-5B">5b</A> Basavaiah D. Rao AJ. Satyanarayana T. Chem. Rev. 2003, 811

<A NAME="RA54509ST-6">6</A> Zhang C. Lu X. J. Org. Chem. 1995, 60: 2906

<A NAME="RA54509ST-7A">7a</A> Trost BM. Dake GR. J. Am. Chem. Soc. 1997, 119: 7595

<A NAME="RA54509ST-7B">7b</A> Trost BM. Li C.-J. J. Am. Chem. Soc. 1994, 116: 10819

<A NAME="RA54509ST-8A">8a</A> Pham TQ. Pyne SG. Skelton BW. White AH. J. Org. Chem. 2005, 70: 6369

<A NAME="RA54509ST-8B">8b</A> Mergott DJ. Frank SA. Roush WR. Org. Lett. 2002, 4: 3157

<A NAME="RA54509ST-8C">8c</A> Mergott DJ. Frank SA. Roush WR. Proc. Natl. Acad. Sci. U.S.A. 2004, 101: 11955

<A NAME="RA54509ST-8D">8d</A> Methot JL. Roush WR. Org. Lett. 2003, 5: 4223

<A NAME="RA54509ST-8E">8e</A> Agapiou K. Krische MJ. Org. Lett. 2003, 5: 1737

<A NAME="RA54509ST-8F">8f</A> Wang J.-C. Krische MJ. Angew. Chem. Int. Ed. 2003, 42: 5855

<A NAME="RA54509ST-8G">8g</A> Du Y. Lu X. J. Org. Chem. 2003, 68: 6463

<A NAME="RA54509ST-8H">8h</A> Tran YS. Kwon O. Org. Lett. 2005, 7: 4289

<A NAME="RA54509ST-8I">8i</A> Jones RA. Krische MJ. Org. Lett. 2009, 11: 1849

<A NAME="RA54509ST-9A">9a</A> Krafft ME. Haxell TFN. J. Am. Chem. Soc. 2005, 127: 10168

<A NAME="RA54509ST-9B">9b</A> Tejedor D. Santos-Exposito A. Mendez-Abt G. Ruiz-Perez C. Garcia-Tellado F. Synlett 2009, 1223

<A NAME="RA54509ST-10">10</A> Evans CA. Miller SJ. J. Am. Chem. Soc. 2003, 125: 12394

<A NAME="RA54509ST-11A">11a</A> Melchiorre P. Marigo M. Carlone A. Bartoli G. Angew. Chem. Int. Ed. 2008, 47: 6138

<A NAME="RA54509ST-11B">11b</A> Akiyama T. Chem. Rev. 2007, 107: 5744

<A NAME="RA54509ST-11C">11c</A> Pellissier H. Tetrahedron 2007, 63: 9267

<A NAME="RA54509ST-11D">11d</A> Masson G. Housseman C. Zhu J. Angew. Chem. Int. Ed. 2007, 46: 4614

<A NAME="RA54509ST-11E">11e</A> Dalko PI. Moisan L. Angew. Chem. Int. Ed. 2004, 43: 5138

<A NAME="RA54509ST-11F">11f</A> Seayad J. List B. Org. Biomol. Chem. 2005, 3: 719

<A NAME="RA54509ST-12A">12a</A> Buono G. Chiodi O. Wills M. Synlett 1999, 377

<A NAME="RA54509ST-12B">12b</A> Gröger H. Burda E. In Phosphorus Ligands in Asymmetric Catalysis Vol. 3: Börner A. Wiley-VCH; Weinheim: 2008. p.1175-1197

<A NAME="RA54509ST-13">13</A> Vedejs E. Daugulis O. Diver ST. J. Org. Chem. 1996, 61: 430

<A NAME="RA54509ST-14">14</A> Zhu G. Chen Z. Jiang Q. Xiao D. Cao P. Zhang X.
J. Am. Chem. Soc. 1997, 119: 3836

<A NAME="RA54509ST-15">15</A> Hayase T. Shibata T. Soai K. Wakatsuki Y. Chem. Commun. (Cambridge) 1998, 1271

<A NAME="RA54509ST-16">16</A> Cho C.-W. Kong J.-R. Krische MJ. Org. Lett. 2004, 6: 1337

<A NAME="RA54509ST-17">17</A> Zhu X.-F. Lan J. Kwon O. J. Am. Chem. Soc. 2003, 125: 4716

<A NAME="RA54509ST-18">18</A> Wallace DJ. Sidda RL. Reamer RA. J. Org. Chem. 2007, 72: 1051

<A NAME="RA54509ST-19">19</A> Chung Y.-K. Fu GC. Angew. Chem. Int. Ed. 2009, 48: 2225

<A NAME="RA54509ST-20">20</A> Roth F. Gygax P. Frater G. Tetrahedron Lett. 1992, 33: 1045

<A NAME="RA54509ST-21">21</A> Jean L. Marinetti A. Tetrahedron Lett. 2006, 47: 2141

<A NAME="RA54509ST-22">22</A> Pereira SI. Adrio J. Silva AMS. Carretero JC.
J. Org. Chem. 2005, 70: 10175

<A NAME="RA54509ST-23">23</A> Wurz RP. Fu GC. J. Am. Chem. Soc. 2005, 127: 12234

<A NAME="RA54509ST-24">24</A> Sampath M. Loh T.-P. Chem. Commun. (Cambridge) 2009, 1568

<A NAME="RA54509ST-25">25</A> Ibrahim AA. Harzmann GD. Kerrigan NJ. J. Org. Chem. 2009, 74: 1777

<A NAME="RA54509ST-26A">26a</A> Vedejs E. Daugulis O. J. Am. Chem. Soc. 1999, 121: 5813

<A NAME="RA54509ST-26B">26b</A> Vedejs E. Daugulis O. J. Am. Chem. Soc. 2003, 125: 4166

<A NAME="RA54509ST-26C">26c</A> Shaw SA. Aleman P. Vedejs E. J. Am. Chem. Soc. 2003, 125: 13368

<A NAME="RA54509ST-26D">26d</A> MacKay JA. Vedejs E. J. Org. Chem. 2006, 71: 498

<A NAME="RA54509ST-27">27</A> Pakulski Z. Demchuk OM. Frelek J. Luboradzki R. Pietrusiewicz KM. Eur. J. Org. Chem. 2004, 3913

<A NAME="RA54509ST-28">28</A> Zhu S.-F. Yang Y. Wang L.-X. Liu B. Zhou Q.-L. Org. Lett. 2005, 7: 2333

<A NAME="RA54509ST-29">29</A> Wilson JE. Fu GC. Angew. Chem. Int. Ed. 2006, 45: 1426

<A NAME="RA54509ST-30A">30a</A> Fleury-Brégeot N. Jean L. Retailleau P. Marinetti A. Tetrahedron 2007, 63: 11920

<A NAME="RA54509ST-30B">30b</A> Pinto N. Fleury-Brégeot N. Marinetti A. Eur. J. Org. Chem. 2009, 146

<A NAME="RA54509ST-31A">31a</A> Gladiali S. Dore A. Fabbri D. De Lucchi O. Manassero M. Tetrahedron: Asymmetry 1994, 5: 511

<A NAME="RA54509ST-31B">31b</A> Enthaler S. Erre G. Junge K. Holz J. Börner A. Alberico E. Nieddu I. Gladiali S. Beller M. Org. Process Res. Dev. 2007, 11: 568

<A NAME="RA54509ST-32A">32a</A> Voituriez A. Panossian A. Fleury-Brégeot N. Retailleau P. Marinetti A. J. Am. Chem. Soc. 2008, 130: 14030

<A NAME="RA54509ST-32B">32b</A> Voituriez A. Panossian A. Fleury-Brégeot N. Retailleau P. Marinetti A. Adv. Synth. Catal. 2009, 351: 1968

<A NAME="RA54509ST-33">33</A> Arrayas RG. Adrio J. Carretero JC. Angew. Chem. Int. Ed. 2006, 45: 7674

<A NAME="RA54509ST-34">34</A> As far as we know, only chiral ferrocenophanes bearing carbon tethers between the Cp rings and attached phosphine functionalities have been prepared so far. For example, see: Sturm T. Weissensteiner W. Spindler F. Mereiter K. Lopez-Agenjo AM. Manzano BR. Jalon FA. Organometallics 2002, 21: 1766

<A NAME="RA54509ST-35">35</A> Fleury-Brégeot N. Panossian A. Chiaroni A. Marinetti A. Eur. J. Inorg. Chem. 2007, 3853

<A NAME="RA54509ST-36">36</A> Hayashi T. Mise T. Fukushima M. Kagotani M. Nagashima N. Hamada Y. Matsumoto A. Kawakami S. Konishi M. Yamamoto K. Kumada M. Bull. Chem. Soc. Jpn. 1980, 53: 1138

<A NAME="RA54509ST-37A">37a</A> Ganter C. Wagner T. Chem. Ber. 1995, 128: 1157

<A NAME="RA54509ST-37B">37b</A> Pugin B, Feng XD, and Thommen M. inventors; WO 2006/003195. (Solvias AG, Switzerland)

<A NAME="RA54509ST-38A">38a</A> Shi M. Chen L.-H. Chem. Commun. (Cambridge) 2003, 1310

<A NAME="RA54509ST-38B">38b</A> Shi M. Chen L.-H. Li C.-Q. J. Am. Chem. Soc. 2005, 127: 3790

<A NAME="RA54509ST-38C">38c</A> Lei Z.-Y. Ma G.-N. Shi M. Eur. J. Org. Chem. 2008, 3817

<A NAME="RA54509ST-38D">38d</A> Shi M. Chen L.-H. Teng W.-D. Adv. Synth. Catal. 2005, 347: 1781

<A NAME="RA54509ST-38E">38e</A> Liu Y.-H. Shi M. Adv. Synth. Catal. 2008, 350: 122

<A NAME="RA54509ST-39">39</A> Matsui K. Takizawa S. Sasai H. Synlett 2006, 761

<A NAME="RA54509ST-40">40</A> Liu Y.-H. Chen L.-H. Shi M. Adv. Synth. Catal. 2006, 348: 973

<A NAME="RA54509ST-41">41</A> Garnier J.-M. Anstiss C. Liu F. Adv. Synth. Catal. 2009, 351: 331

<A NAME="RA54509ST-42">42</A> Ito K. Nishida K. Gotanda T. Tetrahedron Lett. 2007, 48: 6147

<A NAME="RA54509ST-43A">43a</A> Qi M.-J. Ai T. Shi M. Li G. Tetrahedron 2008, 64: 1181

<A NAME="RA54509ST-43B">43b</A> Guan X.-Y. Jiang Y.-Q. Shi M. Eur. J. Org. Chem. 2008, 2150

<A NAME="RA54509ST-44">44</A> Shi Y.-L. Shi M. Adv. Synth. Catal. 2007, 349: 2129

<A NAME="RA54509ST-45">45</A> Yuan K. Zhang L. Song H.-L. Hu Y. Wu X.-Y. Tetrahedron Lett. 2008, 49: 6262

<A NAME="RA54509ST-46">46</A> Cowen BJ. Miller SJ. J. Am. Chem. Soc. 2007, 129: 10988

<A NAME="RA54509ST-47">47</A> Fang Y.-Q. Jacobsen EN. J. Am. Chem. Soc. 2008, 130: 5660

<A NAME="RA54509ST-48A">48a</A> Vedejs E. Diver ST. J. Am. Chem. Soc. 1993, 115: 3358

<A NAME="RA54509ST-48B">48b</A> Vedejs E. MacKay JA. Org. Lett. 2001, 3: 535

<A NAME="RA54509ST-48C">48c</A> MacKay JA. Vedejs E. J. Org. Chem. 2004, 69: 6934

<A NAME="RA54509ST-48D">48d</A> Vedejs E. Rozners E. J. Am. Chem. Soc. 2001, 123: 2428

<A NAME="RA54509ST-49">49</A> Vedejs E. Daugulis O. Tuttle N. J. Org. Chem. 2004, 69: 1389

<A NAME="RA54509ST-50">50</A> Shaw SA. Aleman P. Christy J. Kampf JW. Va P. Vedejs E. J. Am. Chem. Soc. 2006, 128: 925

<A NAME="RA54509ST-51">51</A> Bertenshaw S. Kahn M. Tetrahedron Lett. 1989, 30: 2731

<A NAME="RA54509ST-52A">52a</A> Li W. Zhang Z. Xiao D. Zhang X. J. Org. Chem. 2000, 65: 3489

<A NAME="RA54509ST-52B">52b</A> Lei Z.-Y. Liu X.-G. Shi M. Zhao M. Tetrahedron: Asymmetry 2008, 19: 2058

<A NAME="RA54509ST-53A">53a</A> Shi M. Li C.-Q. Tetrahedron: Asymmetry 2005, 16: 1385

<A NAME="RA54509ST-53B">53b</A> Shi M. Ma G.-N. Gao J. J. Org. Chem. 2007, 72: 9779

<A NAME="RA54509ST-54A">54a</A> Xu Z. Lu X. Tetrahedron Lett. 1997, 38: 3461

<A NAME="RA54509ST-54B">54b</A> Xu Z. Lu X. J. Org. Chem. 1998, 63: 5031

<A NAME="RA54509ST-55">55</A> Zhang B. He Z. Xu S. Wu G. He Z. Tetrahedron 2008, 64: 9471

<A NAME="RA54509ST-56A">56a</A> Castellano S. Fiji HDG. Kinderman SS. Watanabe M. de Leon P. Tamanoi F. Kwon O. J. Am. Chem. Soc. 2007, 129: 5843

<A NAME="RA54509ST-56B">56b</A> Watanabe M. Fiji HDG. Guo L. Chan L. Kinderman SS. Slamon DJ. Kwon O. Tamanoi F. J. Biol. Chem. 2008, 283: 9571

<A NAME="RA54509ST-57A">57a</A> Zhao G.-L. Huang J.-W. Shi M. Org. Lett. 2003, 5: 4737

<A NAME="RA54509ST-57B">57b</A> Zhao G.-L. Shi M. J. Org. Chem. 2005, 70: 9975

<A NAME="RA54509ST-58">58</A> Scherer A. Gladysz JA. Tetrahedron Lett. 2006, 47: 6335

<A NAME="RA54509ST-59">59</A> Zhu X.-F. Henry CE. Kwon O. Tetrahedron 2005, 61: 6276

<A NAME="RA54509ST-60">60</A> Pinto N. Neel M. Panossian A. Retailleau P. Frison G. Voituriez A. Marinetti A. Chem. Eur. J. 2009, in press

For recent mechanistic studies on [3+2] cyclizations, see:

<A NAME="RA54509ST-61A">61a</A> Dudding T. Kwon O. Mercier E. Org. Lett. 2006, 8: 3643

<A NAME="RA54509ST-61B">61b</A> Xia Y. Liang Y. Chen Y. Wang M. Jiao L. Huang F. Liu S. Li Y. Yu Z.-X. J. Am. Chem. Soc. 2007, 129: 3470

<A NAME="RA54509ST-61C">61c</A> Liang Y. Liu S. Xia Y. Li Y. Yu Z.-X. Chem. Eur. J. 2008, 14: 4316

<A NAME="RA54509ST-61D">61d</A> Zhu X.-F. Henry CE. Kwon O. J. Am. Chem. Soc. 2007, 129: 6722

<A NAME="RA54509ST-62">62</A> Du Y. Lu X. Yu Y. J. Org. Chem. 2002, 67: 8901

<A NAME="RA54509ST-63">63</A> Panossian A. Fleury-Brégeot N. Marinetti A. Eur. J. Org. Chem. 2008, 3826

<A NAME="RA54509ST-64A">64a</A> Trost BM. Li C.-J. J. Am. Chem. Soc. 1994, 116: 3167

<A NAME="RA54509ST-64B">64b</A> Zhang C. Lu X. Synlett 1995, 645

<A NAME="RA54509ST-65">65</A> Chen Z. Zhu G. Jiang Q. Xiao D. Cao P. Zhang X. J. Org. Chem. 1998, 63: 5631

<A NAME="RA54509ST-66">66</A> Cho C.-W. Krische MJ. Angew. Chem. Int. Ed. 2004, 43: 6689

<A NAME="RA54509ST-67A">67a</A> Ma G.-N. Cao S.-H. Shi M. Tetrahedron: Asymmetry 2009, 20: 1086

<A NAME="RA54509ST-67B">67b</A> Zhang T.-Z. Dai L.-X. Hou X.-L. Tetrahedron: Asymmetry 2007, 18: 1990

<A NAME="RA54509ST-68">68</A> Jiang Y.-Q. Shi Y.-L. Shi M. J. Am. Chem. Soc. 2008, 130: 7202

<A NAME="RA54509ST-69A">69a</A> Wang L.-C. Luis AL. Agapiou K. Jang H.-Y. Krische MJ. J. Am. Chem. Soc. 2002, 124: 2402

<A NAME="RA54509ST-69B">69b</A> Frank SA. Mergott DJ. Roush WR. J. Am. Chem. Soc. 2002, 124: 2404

<A NAME="RA54509ST-70A">70a</A> Couturier M. Ménard F. Ragan JA. Riou M. Dauphin E. Andresen BM. Ghosh A. Dupont-Gaudet K. Girardin M. Org. Lett. 2004, 6: 1857

<A NAME="RA54509ST-70B">70b</A> Seidel F. Gladysz JA. Synlett 2007, 986

<A NAME="RA54509ST-71">71</A> Aroyan CE. Miller SJ. J. Am. Chem. Soc. 2007, 129: 256

<A NAME="RA54509ST-72">72</A> Mita T. Jacobsen EN. Synlett 2009, 1680