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Muniz, K.: 2018 Science of Synthesis, 2017/4: Catalytic Oxidation in Organic Synthesis DOI: 10.1055/sos-SD-225-00134
Catalytic Oxidation in Organic Synthesis

5.1 Epoxidation of Alkenes

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Editor: Muniz, K.

Authors: Andries-Ulmer, A.; Bellina, F.; Berkessel, A.; Borrell, M.; Caballero, A.; Calleja, P.; Chemler, S.; Chen, P.; Costas, M.; Díaz-Requejo, M. M.; Dorel, R.; Dornan, L.; Ebner, D.; Echavarren, A. M.; Engler, H.; Esguerra, K.; Farràs, P.; Funes, I.; Garrido, P.; Gimbert-Suriñach, C.; Gómez-Arrayas, R.; Griesbeck, A. G. ; Gulder, T.; Hughes, N.; Ikariya, T.; Ishihara, K. ; Jiao, N.; Kayaki, Y. ; Kleczka, M.; Leuther, T.; Li, Z.; Liu, G.; Llobet, A.; Lumb, J.-P.; Martínez, C.; Maseras, F. ; Muldoon, M.; Muniz, K.; Park, N.; Patel, H.; Perego, L.; Pérez, P.; Race, N.; Rodríguez, Nú.; Sigman, M. S.; Sillner, S.; Singh, F. V. ; Stoltz, B. ; Uyanik, M. ; Vicens, L.; Wdowik, T.; Wirth, T.; Wright, A.

Title: Catalytic Oxidation in Organic Synthesis

Print ISBN: 9783132012318; Online ISBN: 9783132403710; Book DOI: 10.1055/b-003-129345

1st edition © 2018 Georg Thieme Verlag KG
Georg Thieme Verlag KG, Stuttgart

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

Science of Synthesis Reference Libraries



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Koch, G.; Molander, G. A.; Schaumann, E.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.

Type: Multivolume Edition

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Abstract

The Sharpless, Jacobsen/Katsuki, and Shi epoxidations are frequently applied in the asymmetric epoxidation of relatively electron-rich alkenes. The development and application of these “classics” has been reviewed numerous times. This chapter covers recent advances in the field, e.g. with regard to the extension of asymmetric epoxidation catalysis to hitherto problematic substrate classes, such as non-conjugated terminal alkenes, or homo- and bis-homoallylic alcohols. At the same time, hydrogen peroxide continues to receive increasing attention as an environmentally friendly and economically attractive terminal oxidant. Examples of efficient organocatalytic epoxidation processes are summarized as well. For electron-poor alkenes, e.g. those carrying carbonyl, nitrile, or sulfone acceptor groups, quite remarkable progress has recently been made both in metal and organocatalysis, and the chapter also includes details of methods and protocols in this area.

Key words

alkenes - oxidation - oxiranes - epoxidation - catalysts - enantioselectivity - iron catalysis - manganese catalysis - ruthenium catalysis - titanium catalysis - tungsten catalysis - vanadium catalysis - zirconium catalysis - organocatalysis - enzyme catalysis
 
  • 1 Cangönül A, Behlendorf M, Gansäuer A, van Gastel M,. Inorg. Chem. 2013; 52: 11859
  • 2 Matsumoto K, Katsuki T, Arends I W C E, In Science of Synthesis: Stereoselective Synthesis. de Vries J G. Thieme; Stuttgart 2011. Vol.  1, Section 1.2.1.1, p  70.
    Google Scholar
  • 3 Matsumoto K, Katsuki T, Arends I W C E, In Science of Synthesis: Stereoselective Synthesis. de Vries J G. Thieme; Stuttgart 2011. Vol.  1, Section 1.2.2.1, p  82.
    Google Scholar
  • 4 Matsumoto K, Katsuki T, Arends I W C E, In Science of Synthesis: Stereoselective Synthesis. de Vries J G. Thieme; Stuttgart 2011. Vol.  1, Section 1.2.2.7.2, p  105.
    Google Scholar
  • 5 Matsumoto K, Katsuki T, Arends I W C E, In Science of Synthesis: Stereoselective Synthesis. de Vries J G. Thieme; Stuttgart 2011. Vol.  1, Section 1.2, p  69.
    Google Scholar
  • 6 Xia F, Ye S, In Science of Synthesis: Metal-Catalyzed Cyclization Reactions. Ma S, Gao S. Thieme; Stuttgart 2016. Vol.  2, Section 2.1, p  1.
    Google Scholar
  • 7 Adolfsson H, In Science of Synthesis. Forsyth C J, Jacobsen E N. 2008. Vol.  37, Section 37.2.1, p  227.
    Google Scholar
  • 8 Goeddel D, Shi Y, In Science of Synthesis. Forsyth C J, Jacobsen E N. 2008. Vol.  37, Section 37.2.2, p  277.
    Google Scholar
  • 9 Sawada Y, Matsumoto K, Kondo S, Watanabe H, Ozawa T, Suzuki K, Saito B, Katsuki T. Angew. Chem. Int. Ed. 2006; 45: 3478
  • 10 Talsi E P, Samsonenko D G, Bryliakov K P. Chem.–Eur. J. 2014; 20: 14329
  • 11 Jat J L, De S R, Kumar G, Adebesin A M, Gandham S K, Falck J R. Org. Lett. 2015; 17: 1058
  • 12 Larivee A, Unger J B, Thomas M, Wirtz C, Dubost C, Handa S, Fürstner A. Angew. Chem. Int. Ed. 2011; 50: 304
  • 13 Matsumoto K, Sawada Y, Saito B, Sakai K, Katsuki T. Angew. Chem. Int. Ed. 2005; 44: 4935
  • 14 Xiong D, Hu X, Wang S, Miao C, Xia C, Sun W. Eur. J. Org. Chem. 2011; 4289
  • 15 Matsumoto K, Feng C, Handa S, Oguma T, Katsuki T. Tetrahedron 2011; 67: 6474
  • 16 Eckert P K, Schill V, Strohmann C. Inorg. Chim. Acta 2011; 376: 634
  • 17 Berkessel A, Ong M-C, Nachi M, Neudörfl J-M. ChemCatChem 2010; 2: 1215
  • 18 Berkessel A, Günther T, Wang Q, Neudörfl J-M. Angew. Chem. Int. Ed. 2013; 52: 8467
  • 19 Wang Q, Neudörfl J-M, Berkessel A. Chem.–Eur. J. 2015; 21: 247
  • 20 Lansing M, Engler H, Leuther T M, Neudörfl J-M, Berkessel A. ChemCatChem 2016; 8: 3706
  • 21 Talsi E P, Bryliakova A A, Bryliakov K P. Chem. Rec. 2016; 16: 924
  • 22 Amiri N, Le Maux P, Srour H, Nasri H, Simonneaux G. Tetrahedron 2014; 70: 8836
  • 23 Le Maux P, Srour H F, Simonneaux G. Tetrahedron 2012; 68: 5824
  • 24 Francis M B, Jacobsen E N. Angew. Chem. Int. Ed. 1999; 38: 937
  • 25 Gelalcha F G, Gopinatan A, Bitterlich B, Tse M K, Beller M. Angew. Chem. Int. Ed. 2007; 46: 7293
  • 26 Cussó O, Ribas X, Costas M. Chem. Commun. (Cambridge) 2015; 51: 14285
  • 27 De Faveri G, Ilyashenko G, Watkinson M. Chem. Soc. Rev. 2011; 40: 1722
  • 28 Chen Z, Yin G. Chem. Soc. Rev. 2015; 44: 1083
  • 29 Darwish M, Wills M. Catal. Sci. Technol. 2012; 2: 243
  • 30 Fingerhut A, Serdyuk O V, Tsogoeva S B. Green Chem. 2015; 17: 2042
  • 31 Bryliakov K P, Talsi E P. Coord. Chem. Rev. 2014; 276: 73
  • 32 McDonald A R, Que Jr. L. Coord. Chem. Rev. 2013; 257: 414
  • 33 Talsi E P, Bryliakov K P. Coord. Chem. Rev. 2012; 256: 1418
  • 34 Yeung H-L, Sham K-C, Tsang C-S, Lau T-C, Kwong H-L. Chem. Commun. (Cambridge) 2008; 3801
  • 35 Cussó O, Garcia-Bosch I, Ribas X, Lloret-Fillol J, Costas M. J. Am. Chem. Soc. 2013; 135: 14871
  • 36 Lyakin O Y, Ottenbacher R V, Bryliakov K P, Talsi E P. ACS Catal. 2012; 2: 1196
  • 37 Cussó O, Ribas X, Lloret-Fillol J, Costas M. Angew. Chem. Int. Ed. 2015; 54: 2729
  • 38 Lyakin O Y, Bryliakov K P, Britovsek G J P, Talsi E P. J. Am. Chem. Soc. 2009; 131: 10798
  • 39 Lyakin O Y, Bryliakov K P, Talsi E P. Inorg. Chem. 2011; 50: 5526
  • 40 Wang Y, Janardanan D, Usharani D, Han K, Que Jr. L, Shaik S. ACS Catal. 2013; 3: 1334
  • 41 Oloo W N, Meier K K, Wang Y, Shaik S, Münck E, Que Jr. L. Nat. Commun. 2014; 5: 3046
  • 42 Oloo W N, Que Jr. L. Acc. Chem. Res. 2015; 48: 2612
  • 43 Lyakin O Y, Zima A M, Samsonenko D G, Bryliakov K P, Talsi E P. ACS Catal. 2015; 5: 2702
  • 44 Zhang W, Loebach J L, Wilson S R, Jacobsen E N. J. Am. Chem. Soc. 1990; 112: 2801
  • 45 Shi Q-P, Shi Z-H, Li N-G, Tang Y-P, Li W, Tang H, Zhang W, Shen M-Z, Duan J-A. Curr. Org. Chem. 2013; 17: 2936
  • 46 Shi Z-H, Li N-G, Shi Q-P, Tang Y-P, Tang H, Shen M-Z, Duan J-A. Curr. Org. Chem. 2014; 11: 204
  • 47 Cheng T, Zhao Q, Zhang D, Liu G. Green Chem. 2015; 17: 2100
  • 48 Krishnan K K, Thomas A M, Sindhu K S, Anilkumar G. Tetrahedron 2016; 72: 1
  • 49 Saisaha P, de Boer J W, Browne W R. Chem. Soc. Rev. 2013; 42: 2059
  • 50 Teixeira F, Cordeiro M N D S. Catalysts 2017; 7: 2
  • 51 Hughes D L, Smith G B, Liu J, Dezeny G C, Senanayake C H, Larsen R D, Verhoeven T R, Reider P J. J. Org. Chem. 1997; 62: 2222
  • 52 Chen L, Cheng F, Jia L, Wang L, Wei J, Zhang J, Yao L, Tang N, Wu J. Appl. Catal., A 2012; 415–416: 40
  • 53 Ruffo F, Bismuto A, Carpentieri A, Cucciolito M E, Lega M, Tuzi A. Inorg. Chim. Acta 2013; 405: 288
  • 54 Chen L, Wei J, Tang N, Cheng F. Catal. Lett. 2012; 142: 486
  • 55 Liao S, List B. Angew. Chem. Int. Ed. 2010; 49: 628
  • 56 Jacobsen E N, Zhang W, Muci A R, Ecker J R, Deng L. J. Am. Chem. Soc. 1991; 113: 7063
  • 57 Huang X, Fu X, Jia Z, Miao Q, Wang G. Sci. China: Chem. 2013; 56: 604
  • 58 Kureshy R I, Roy T, Khan N-u H, Abdi S H R, Sadhukhan A, Bajaj H C. J. Catal. 2012; 286: 41
  • 59 Huang X, Fu X, Wu X, Jia Z. Tetrahedron Lett. 2013; 54: 4041
  • 60 Huang X, Fu X, Jia Z, Miao Q, Wang G. Catal. Sci. Technol. 2013; 3: 415
  • 61 Maity N C, Abdi S H R, Kureshy R I, Khan N-u H, Suresh E, Dangi G P, Bajaj H C. J. Catal. 2011; 277: 123
  • 62 Konsler R G, Karl J, Jacobsen E N. J. Am. Chem. Soc. 1998; 120: 10780
  • 63 Bogaerts T, Wouters S, Van Der Voort P, Van Speybroeck V. J. Mol. Catal. A: Chem. 2015; 406: 106
  • 64 Kuźniarska-Biernacka I, Silva A R, Carvalho A P, Pires J, Freire C. Catal. Lett. 2009; 134: 63
  • 65 La Paglia Fragola V, Lupo F, Pappalardo A, Trusso Sfrazzetto G, Toscano R M, Ballistreri F P, Tomaselli G A, Gulino A. J. Mater. Chem. 2012; 22: 20561
  • 66 Ji R, Yu K, Lou L-L, Liu S. J. Mol. Catal. A: Chem. 2013; 378: 7
  • 67 Song F, Wang C, Falkowski J M, Ma L, Lin W. J. Am. Chem. Soc. 2010; 132: 15390
  • 68 Wei S, Tang Y, Xu X, Xu G, Yu Y, Sun Y, Zheng Y. Appl. Organomet. Chem. 2011; 25: 146
  • 69 Huang J, Fu X, Wang G, Ge Y, Miao Q. Catal. Sci. Technol. 2012; 2: 1040
  • 70 Huang J, Yuan L, Cai J, Chen X, Qi D. Inorg. Chem. Commun. 2016; 65: 4
  • 71 Feichtinger D, Plattner D A. Angew. Chem. Int. Ed. Engl. 1997; 36: 1718
  • 72 Lee N H, Jacobsen E N. Tetrahedron Lett. 1991; 32: 6533
  • 73 Linde C, Arnold M, Åkermark B, Norrby P-O. Angew. Chem. Int. Ed. Engl. 1997; 36: 1723
  • 74 Linker T. Angew. Chem. Int. Ed. Engl. 1997; 36: 2060
  • 75 Fu H, Look G C, Zhang W, Jacobsen E N, Wong C H. J. Org. Chem. 1991; 56: 6497
  • 76 Linde C, Koliaï N, Norrby P-O, Åkermark B. Chem.–Eur. J. 2002; 8: 2568
  • 77 Dai W, Li J, Li G, Yang H, Wang L, Gao S. Org. Lett. 2013; 15: 4138
  • 78 Dai W, Shang S, Chen B, Li G, Wang L, Ren L, Gao S. J. Org. Chem. 2014; 79: 6688
  • 79 Shen D, Qiu B, Xu D, Miao C, Xia C, Sun W. Org. Lett. 2016; 18: 372
  • 80 Farokhi A, Hosseini-Monfared H. New J. Chem. 2016; 40: 5032
  • 81 Ottenbacher R V, Bryliakov K P, Talsi E P. Inorg. Chem. 2010; 49: 8620
  • 82 Groves J T, Lee J B, Marla S S. J. Am. Chem. Soc. 1997; 119: 6269
  • 83 Ottenbacher R V, Samsonenko D G, Talsi E P, Bryliakov K P. ACS Catal. 2014; 4: 1599
  • 84 Ottenbacher R V, Samsonenko D G, Talsi E P, Bryliakov K P. ACS Catal. 2016; 6: 979
  • 85 Lai T-S, Zhang R, Cheung K-K, Kwong H-L, Che C-M. Chem. Commun. (Cambridge) 1998; 1583
  • 86 Döbler C, Mehltretter G, Beller M. Angew. Chem. Int. Ed. 1999; 38: 3026
  • 87 Koya S, Nishioka Y, Mizoguchi H, Uchida T, Katsuki T. Angew. Chem. Int. Ed. 2012; 51: 8243
  • 88 Uchida T, Katsuki T. J. Synth. Org. Chem., Jpn. 2013; 71: 1126
  • 89 Fackler P, Berthold C, Voss F, Bach T. J. Am. Chem. Soc. 2010; 132: 15911
  • 90 Fackler P, Huber S M, Bach T. J. Am. Chem. Soc. 2012; 134: 12869
  • 91 Wong O A, Shi Y. Chem. Rev. 2008; 108: 3958
  • 92 Wong O A, Ramirez T A, Shi Y, In Science of Synthesis: Asymmetric Organocatalysis. List B. Thieme; Stuttgart 2012. Vol.  1, Section 1.2.1, p  783.
    Google Scholar
  • 93 Vega-Pérez J M, Vega-Holm M, Periñán I, Palo-Nieto C, Iglesias-Guerra F. Tetrahedron 2011; 67: 364
  • 94 Vega-Pérez J M, Periñán I, Vega-Holm M, Palo-Nieto C, Iglesias-Guerra F. Tetrahedron 2011; 67: 7057
  • 95 Day D P, Sellars P B. Eur. J. Org. Chem. 2017; 1034
  • 96 Bulman Page P C, Bartlett C J, Chan Y, Allin S M, McKenzie M J, Lacour J, Jones G A. Org. Biomol. Chem. 2016; 14: 4220
  • 97 Bulman Page P C, Appleby L F, Day D, Chan Y, Buckley B R, Allin S M, McKenzie M J. Org. Lett. 2009; 11: 1991
  • 98 Bulman Page P C, Buckley B R, Barros D, Blacker A J, Heaney H, Marples B A. Tetrahedron 2006; 62: 6607
  • 99 Bartlett C J, Day D P, Chan Y, Allin S M, McKenzie M J, Slawin A M Z, Bulman Page P C. J. Org. Chem. 2012; 77: 772
  • 100 Bulman Page P C, Buckley B R, Farah M M, Blacker A J. Eur. J. Org. Chem. 2009; 3413
  • 101 Fasan R. ACS Catal. 2012; 2: 647
  • 102 Hrycay E G, Bandiera S M. Adv. Exp. Med. Biol. 2015; 851: 1
  • 103 Li A T, Li Z, In Science of Synthesis: Biocatalysis in Organic Synthesis. Faber K, Fessner W-D, Turner N J. Thieme; Stuttgart 2015. Vol.  2, Section 2.6, p  479.
    Google Scholar
  • 104 Bühler B, Bühler K, Hollmann F, In Enzyme Catalysis in Organic Synthesis. Drauz K, Gröger H, May O. Wiley-VCH; Weinheim, Germany 2012. Vol.  3, p  1278.
    Google Scholar
  • 105 Carballeira J D, Quezada M A, Hoyos P, Simeó Y, Hernaiz M J, Alcantara A R, Sinisterra J V. Biotechnol. Adv. 2009; 27: 686
  • 106 Li A, Liu J, Pham S Q, Li Z. Chem. Commun. (Cambridge) 2013; 49: 11572
  • 107 Wang B, Li C, Dubey K D, Shaik S. J. Am. Chem. Soc. 2015; 137: 7379
  • 108 Lin H, Liu J-Y, Wang H-B, Ahmed A A Q, Wu Z-L. J. Mol. Catal. B: Enzym. 2011; 72: 77
  • 109 Kuhn D, Kholiq M A, Heinzle E, Bühler B, Schmid A. Green Chem. 2010; 12: 815
  • 110 Lin H, Qiao J, Liu Y, Wu Z-L. J. Mol. Catal. B: Enzym. 2010; 67: 236
  • 111 Minami A, Shimaya M, Suzuki G, Migita A, Shinde S S, Sato K, Watanabe K, Tamura T, Oguri H, Oikawa H. J. Am. Chem. Soc. 2012; 134: 7246
  • 112 Wu J, Liu C, Jiang Y, Hu M, Li S, Zhai Q. Catal. Commun. 2010; 11: 727
  • 113 Ramón D J, Yus M. Chem. Rev. 2006; 106: 2126
  • 114 Katsuki T, Martin V S. Org. React. (N. Y.) 1995; 48: 1
  • 115 Heravi M M, Lashaki T B, Poorahmad N. Tetrahedron: Asymmetry 2015; 26: 405
  • 116 Ji N, Yuan J, Liu M, Lan T, He W. Chem. Commun. (Cambridge) 2016; 52: 7731
  • 117 Li Z, Yamamoto H. Acc. Chem. Res. 2013; 46: 506
  • 118 Olivares-Romero J L, Li Z, Yamamoto H. J. Am. Chem. Soc. 2013; 135: 3411
  • 119 Li Z, Yamamoto H. J. Am. Chem. Soc. 2010; 132: 7878
  • 120 Olivares-Romero J L, Li Z, Yamamoto H. J. Am. Chem. Soc. 2012; 134: 5440
  • 121 Licini G, Conte V, Coletti A, Mba M, Zonta C. Coord. Chem. Rev. 2011; 255: 2345
  • 122 Noji M, Kobayashi T, Uechi Y, Kikuchi A, Kondo H, Sugiyama S, Ishii K. J. Org. Chem. 2015; 80: 3203
  • 123 Wang C, Yamamoto H. J. Am. Chem. Soc. 2014; 136: 1222
  • 124 Murphy A, Dubois G, Stack T D P. J. Am. Chem. Soc. 2003; 125: 5250
  • 125 Murphy A, Pace A, Stack T D P. Org. Lett. 2004; 6: 3119
  • 126 Murphy A, Stack T D P. J. Mol. Catal. A: Chem. 2006; 251: 78
  • 127 Wang B, Miao C, Wang S, Xia C, Sun W. Chem.–Eur. J. 2012; 18: 6750
  • 128 Wang X, Miao C, Wang S, Xia C, Sun W. ChemCatChem 2013; 5: 2489
  • 129 Shen D, Miao C, Wang S, Xia C, Sun W. Eur. J. Inorg. Chem. 2014; 5777
  • 130 Sin N, Kim K B, Elofsson M, Meng L, Auth H, Kwok B H B, Crews C M. Bioorg. Med. Chem. Lett. 1999; 9: 2283
  • 131 Cussó O, Garcia-Bosch I, Font D, Ribas X, Lloret-Fillol J, Costas M. Org. Lett. 2013; 15: 6158
  • 132 White M C, Doyle A G, Jacobsen E N. J. Am. Chem. Soc. 2001; 123: 7194
  • 133 Gopalaiah K. Chem. Rev. 2013; 113: 3248
  • 134 Gelalcha F G. Adv. Synth. Catal. 2014; 356: 261
  • 135 Wang C, Yamamoto H. Chem.–Asian J. 2015; 10: 2056
  • 136 Dai W, Li G, Chen B, Wang L, Gao S. Org. Lett. 2015; 17: 904
  • 137 Wang B, Wang S, Xia C, Sun W. Chem.–Eur. J. 2012; 18: 7332
  • 138 Nishikawa Y, Yamamoto H. J. Am. Chem. Soc. 2011; 133: 8432
  • 139 Luo L, Yamamoto H. Eur. J. Org. Chem. 2014; 7803
  • 140 Cussó O, Cianfanelli M, Ribas X, Klein Gebbink R J M, Costas M. J. Am. Chem. Soc. 2016; 138: 2732
  • 141 Bougauchi M, Watanabe S, Arai T, Sasai H, Shibasaki M. J. Am. Chem. Soc. 1997; 119: 2329
  • 142 Nemoto T, Ohshima T, Yamaguchi K, Shibasaki M. J. Am. Chem. Soc. 2001; 123: 2725
  • 143 Kakei H, Tsuji R, Ohshima T, Shibasaki M. J. Am. Chem. Soc. 2005; 127: 8962
  • 144 Colonna S, Perdicchia D, In Science of Synthesis: Stereoselective Synthesis. de Vries J G. Thieme; Stuttgart 2011. Vol.  1, Section 1.3, p  123.
    Google Scholar
  • 145 Qian Q, Tan Y, Zhao B, Feng T, Shen Q, Yao Y. Org. Lett. 2014; 16: 4516
  • 146 Chu Y, Liu X, Li W, Hu X, Lin L, Feng X. Chem. Sci. 2012; 3: 1996
  • 147 Chu Y, Hao X, Lin L, Chen W, Li W, Tan F, Liu X, Feng X. Adv. Synth. Catal. 2014; 356: 2214
  • 148 Dandia A, Singh R, Saha M, Shivpuri A. Pharmazie 2002; 57: 602
  • 149 Juliá S, Masana J, Vega J C. Angew. Chem. Int. Ed. Engl. 1980; 19: 929
  • 150 Weiss K M, Tsogoeva S B. Chem. Rec. 2011; 11: 18
  • 151 Zhu Y G, Wang Q, Cornwall R G, Shi Y. Chem. Rev. 2014; 114: 8199
  • 152 Nagano M, Doi M, Kurihara M, Suemune H, Tanaka M. Org. Lett. 2010; 12: 3564
  • 153 Akagawa K, Kudo K. Adv. Synth. Catal. 2011; 353: 843
  • 154 Demizu Y, Yamagata N, Nagoya S, Sato Y, Doi M, Tanaka M, Nagasawa K, Okuda H, Kurihara M. Tetrahedron 2011; 67: 6155
  • 155 Miranda R-A, Llorca J, Medina F, Sueiras J E, Segarra A M. J. Catal. 2011; 282: 65
  • 156 Yamagata N, Demizu Y, Sato Y, Doi M, Tanaka M, Nagasawa K, Okuda H, Kurihara M. Tetrahedron Lett. 2011; 52: 798
  • 157 Akagawa K, Hirata T, Kudo K. Synlett 2016; 27: 1217
  • 158 Weyer A, Díaz D, Nierth A, Schlörer N E, Berkessel A. ChemCatChem 2012; 4: 337
  • 159 Berkessel A, Gasch N, Glaubitz K, Koch C. Org. Lett. 2001; 3: 3839
  • 160 Berkessel A, Koch B, Toniolo C, Rainaldi M, Broxterman Q B, Kaptein B. Biopolymers 2006; 84: 90
  • 161 Wakeham D, Crivoi D G, Medina F, Segarra A M, Rutland M W. J. Colloid Interface Sci. 2016; 469: 263
  • 162 Davis R L, Stiller J, Naicker T, Jiang H, Jørgensen K A. Angew. Chem. Int. Ed. 2014; 53: 7406
  • 163 Meninno S, Lattanzi A. Catal. Today 2017; 285: 39
  • 164 Hashimoto T, Maruoka K. Chem. Rev. 2007; 107: 5656
  • 165 Ooi T, Maruoka K. Angew. Chem. Int. Ed. 2007; 46: 4222
  • 166 Marigo M, Franzén J, Poulsen T B, Zhuang W, Jørgensen K A. J. Am. Chem. Soc. 2005; 127: 6964
  • 167 Lattanzi A. Chem. Commun. (Cambridge) 2009; 1452
  • 168 Lee S, MacMillan D W C. Tetrahedron 2006; 62: 11413
  • 169 Wang X, List B. Angew. Chem. Int. Ed. 2008; 47: 1119
  • 170 Wang X, Reisinger C M, List B. J. Am. Chem. Soc. 2008; 130: 6070
  • 171 Sparr C, Schweizer W B, Senn H M, Gilmour R. Angew. Chem. Int. Ed. 2009; 48: 3065
  • 172 Russo A, Lattanzi A. Org. Biomol. Chem. 2010; 8: 2633
  • 173 De Fusco C, Tedesco C, Lattanzi A. J. Org. Chem. 2011; 76: 676
  • 174 Russo A, Lattanzi A. Synthesis 2009; 1551
  • 175 Zhao G-L, Ibrahem I, Sundén H, Córdova A. Adv. Synth. Catal. 2007; 349: 1210
  • 176 Deobald A M, Corrêa A G, Rivera D G, Paixão M W. Org. Biomol. Chem. 2012; 10: 7681
  • 177 Egger J, Bretscher P, Freigang S, Kopf M, Carreira E M. Angew. Chem. Int. Ed. 2013; 52: 5382
  • 178 Lee A, Reisinger C M, List B. Adv. Synth. Catal. 2012; 354: 1701
  • 179 Lifchits O, Mahlau M, Reisinger C M, Lee A, Fares C, Polyak I, Gopakumar G, Thiel W, List B. J. Am. Chem. Soc. 2013; 135: 6677
  • 180 Lifchits O, Reisinger C M, List B. J. Am. Chem. Soc. 2010; 132: 10227
  • 181 Russo A, Galdi G, Croce G, Lattanzi A. Chem.–Eur. J. 2012; 18: 6152
  • 182 Meninno S, Vidal-Albalat A, Lattanzi A. Org. Lett. 2015; 17: 4348
  • 183 Meninno S, Zullo L, Overgaard J, Lattanzi A. Adv. Synth. Catal. 2017; 359: 913
  • 184 Kawai H, Okusu S, Yuan Z, Tokunaga E, Yamano A, Shiro M, Shibata N. Angew. Chem. Int. Ed. 2013; 52: 2221
  • 185 Wu S, Pan D, Cao C, Wang Q, Chen F-X. Adv. Synth. Catal. 2013; 355: 1917
  • 186 Vidal-Albalat A, Świderek K, Izquierdo J, Rodríguez S, Moliner V, González F V. Chem. Commun. (Cambridge) 2016; 52: 10060
  • 187 Allingham M T, Bennett E L, Davies D H, Harper P M, Howard-Jones A, Mehdar Y T H, Murphy P J, Thomas D A, Caulkett P W R, Potter D, Lam C M, OʼDonoghue A C. Tetrahedron 2016; 72: 496