5.1 Epoxidation of Alkenes

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 IWCE, In: Science of Synthesis: Stereoselective Synthesis de Vries JG. Thieme Stuttgart 2011; 1. 70

• 3 Matsumoto K, Katsuki T, Arends IWCE, In: Science of Synthesis: Stereoselective Synthesis de Vries JG. Thieme Stuttgart 2011; 1. 82

• 4 Matsumoto K, Katsuki T, Arends IWCE, In: Science of Synthesis: Stereoselective Synthesis de Vries JG. Thieme Stuttgart 2011; 1. 105

• 5 Matsumoto K, Katsuki T, Arends IWCE, In: Science of Synthesis: Stereoselective Synthesis de Vries JG. Thieme Stuttgart 2011; 1. 69

• 6 Xia F, Ye S, In: Science of Synthesis: Metal-Catalyzed Cyclization Reactions Ma S, Gao S. Thieme Stuttgart 2016; 2. 1

• 7 Adolfsson H, In: Science of Synthesis Forsyth CJ, Jacobsen EN. 2008; 37. 227

• 8 Goeddel D, Shi Y, In: Science of Synthesis Forsyth CJ, Jacobsen EN. 2008; 37. 277

• 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 EP, Samsonenko DG, Bryliakov KP. Chem.–Eur. J. 2014; 20: 14329

• 11 Jat JL, De SR, Kumar G, Adebesin AM, Gandham SK, Falck JR. Org. Lett. 2015; 17: 1058

• 12 Larivee A, Unger JB, 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 PK, 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 TM, Neudörfl J.-M, Berkessel A. ChemCatChem 2016; 8: 3706

• 21 Talsi EP, Bryliakova AA, Bryliakov KP. 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 HF, Simonneaux G. Tetrahedron 2012; 68: 5824

• 24 Francis MB, Jacobsen EN. Angew. Chem. Int. Ed. 1999; 38: 937

• 25 Gelalcha FG, Gopinatan A, Bitterlich B, Tse MK, 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 OV, Tsogoeva SB. Green Chem. 2015; 17: 2042

• 31 Bryliakov KP, Talsi EP. Coord. Chem. Rev. 2014; 276: 73

• 32 McDonald AR, Que Jr L. Coord. Chem. Rev. 2013; 257: 414

• 33 Talsi EP, Bryliakov KP. 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 OY, Ottenbacher RV, Bryliakov KP, Talsi EP. ACS Catal. 2012; 2: 1196

• 37 Cussó O, Ribas X, Lloret-Fillol J, Costas M. Angew. Chem. Int. Ed. 2015; 54: 2729

• 38 Lyakin OY, Bryliakov KP, Britovsek GJP, Talsi EP. J. Am. Chem. Soc. 2009; 131: 10798

• 39 Lyakin OY, Bryliakov KP, Talsi EP. 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 WN, Meier KK, Wang Y, Shaik S, Münck E, Que Jr L. Nat. Commun. 2014; 5: 3046

• 42 Oloo WN, Que Jr L. Acc. Chem. Res. 2015; 48: 2612

• 43 Lyakin OY, Zima AM, Samsonenko DG, Bryliakov KP, Talsi EP. ACS Catal. 2015; 5: 2702

• 44 Zhang W, Loebach JL, Wilson SR, Jacobsen EN. 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 KK, Thomas AM, Sindhu KS, Anilkumar G. Tetrahedron 2016; 72: 1

• 49 Saisaha P, de Boer JW, Browne WR. Chem. Soc. Rev. 2013; 42: 2059

• 50 Teixeira F, Cordeiro MNDS. Catalysts 2017; 7: 2

• 51 Hughes DL, Smith GB, Liu J, Dezeny GC, Senanayake CH, Larsen RD, Verhoeven TR, Reider PJ. 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 ME, 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 EN, Zhang W, Muci AR, Ecker JR, 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 RI, Roy T, Khan N.-uH, Abdi SHR, Sadhukhan A, Bajaj HC. 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 NC, Abdi SHR, Kureshy RI, Khan N.-uH, Suresh E, Dangi GP, Bajaj HC. J. Catal. 2011; 277: 123

• 62 Konsler RG, Karl J, Jacobsen EN. 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 AR, Carvalho AP, Pires J, Freire C. Catal. Lett. 2009; 134: 63

• 65 La Paglia Fragola V, Lupo F, Pappalardo A, Trusso Sfrazzetto G, Toscano RM, Ballistreri FP, Tomaselli GA, 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 JM, 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 DA. Angew. Chem. Int. Ed. Engl. 1997; 36: 1718

• 72 Lee NH, Jacobsen EN. 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 GC, Zhang W, Jacobsen EN, Wong CH. 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 RV, Bryliakov KP, Talsi EP. Inorg. Chem. 2010; 49: 8620

• 82 Groves JT, Lee JB, Marla SS. J. Am. Chem. Soc. 1997; 119: 6269

• 83 Ottenbacher RV, Samsonenko DG, Talsi EP, Bryliakov KP. ACS Catal. 2014; 4: 1599

• 84 Ottenbacher RV, Samsonenko DG, Talsi EP, Bryliakov KP. 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 SM, Bach T. J. Am. Chem. Soc. 2012; 134: 12869

• 91 Wong OA, Shi Y. Chem. Rev. 2008; 108: 3958

• 92 Wong OA, Ramirez TA, Shi Y, In: Science of Synthesis: Asymmetric Organocatalysis List B. Thieme Stuttgart 2012; 1. 783

• 93 Vega-Pérez JM, Vega-Holm M, Periñán I, Palo-Nieto C, Iglesias-Guerra F. Tetrahedron 2011; 67: 364

• 94 Vega-Pérez JM, Periñán I, Vega-Holm M, Palo-Nieto C, Iglesias-Guerra F. Tetrahedron 2011; 67: 7057

• 95 Day DP, Sellars PB. Eur. J. Org. Chem. 2017; 1034

• 96 Bulman Page PC, Bartlett CJ, Chan Y, Allin SM, McKenzie MJ, Lacour J, Jones GA. Org. Biomol. Chem. 2016; 14: 4220

• 97 Bulman Page PC, Appleby LF, Day D, Chan Y, Buckley BR, Allin SM, McKenzie MJ. Org. Lett. 2009; 11: 1991

• 98 Bulman Page PC, Buckley BR, Barros D, Blacker AJ, Heaney H, Marples BA. Tetrahedron 2006; 62: 6607

• 99 Bartlett CJ, Day DP, Chan Y, Allin SM, McKenzie MJ, Slawin AMZ, Bulman Page PC. J. Org. Chem. 2012; 77: 772

• 100 Bulman Page PC, Buckley BR, Farah MM, Blacker AJ. Eur. J. Org. Chem. 2009; 3413

• 101 Fasan R. ACS Catal. 2012; 2: 647

• 102 Hrycay EG, Bandiera SM. Adv. Exp. Med. Biol. 2015; 851: 1

• 103 Li AT, Li Z, In: Science of Synthesis: Biocatalysis in Organic Synthesis Faber K, Fessner W.-D, Turner NJ. Thieme Stuttgart 2015; 2. 479

• 104 Bühler B, Bühler K, Hollmann F, In: Enzyme Catalysis in Organic Synthesis Drauz K, Gröger H, May O. Wiley-VCH Weinheim, Germany 2012; 3. 1278

• 105 Carballeira JD, Quezada MA, Hoyos P, Simeó Y, Hernaiz MJ, Alcantara AR, Sinisterra JV. Biotechnol. Adv. 2009; 27: 686

• 106 Li A, Liu J, Pham SQ, Li Z. Chem. Commun. (Cambridge) 2013; 49: 11572

• 107 Wang B, Li C, Dubey KD, Shaik S. J. Am. Chem. Soc. 2015; 137: 7379

• 108 Lin H, Liu J.-Y, Wang H.-B, Ahmed AAQ, Wu Z.-L. J. Mol. Catal. B: Enzym. 2011; 72: 77

• 109 Kuhn D, Kholiq MA, 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 SS, 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 DJ, Yus M. Chem. Rev. 2006; 106: 2126

• 114 Katsuki T, Martin VS. Org. React. (N. Y.) 1995; 48: 1

• 115 Heravi MM, Lashaki TB, 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 JL, 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 JL, 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 TDP. J. Am. Chem. Soc. 2003; 125: 5250

• 125 Murphy A, Pace A, Stack TDP. Org. Lett. 2004; 6: 3119

• 126 Murphy A, Stack TDP. 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 KB, Elofsson M, Meng L, Auth H, Kwok BHB, Crews CM. 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 MC, Doyle AG, Jacobsen EN. J. Am. Chem. Soc. 2001; 123: 7194

• 133 Gopalaiah K. Chem. Rev. 2013; 113: 3248

• 134 Gelalcha FG. 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 RJM, 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 JG. Thieme Stuttgart 2011; 1. 123

• 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 JC. Angew. Chem. Int. Ed. Engl. 1980; 19: 929

• 150 Weiss KM, Tsogoeva SB. Chem. Rec. 2011; 11: 18

• 151 Zhu YG, Wang Q, Cornwall RG, 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 JE, Segarra AM. 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 NE, 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 QB, Kaptein B. Biopolymers 2006; 84: 90

• 161 Wakeham D, Crivoi DG, Medina F, Segarra AM, Rutland MW. J. Colloid Interface Sci. 2016; 469: 263

• 162 Davis RL, Stiller J, Naicker T, Jiang H, Jørgensen KA. 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 TB, Zhuang W, Jørgensen KA. J. Am. Chem. Soc. 2005; 127: 6964

• 167 Lattanzi A. Chem. Commun. (Cambridge) 2009; 1452

• 168 Lee S, MacMillan DWC. Tetrahedron 2006; 62: 11413

• 169 Wang X, List B. Angew. Chem. Int. Ed. 2008; 47: 1119

• 170 Wang X, Reisinger CM, List B. J. Am. Chem. Soc. 2008; 130: 6070

• 171 Sparr C, Schweizer WB, Senn HM, 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 AM, Corrêa AG, Rivera DG, Paixão MW. Org. Biomol. Chem. 2012; 10: 7681

• 177 Egger J, Bretscher P, Freigang S, Kopf M, Carreira EM. Angew. Chem. Int. Ed. 2013; 52: 5382

• 178 Lee A, Reisinger CM, List B. Adv. Synth. Catal. 2012; 354: 1701

• 179 Lifchits O, Mahlau M, Reisinger CM, Lee A, Fares C, Polyak I, Gopakumar G, Thiel W, List B. J. Am. Chem. Soc. 2013; 135: 6677

• 180 Lifchits O, Reisinger CM, 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 FV. Chem. Commun. (Cambridge) 2016; 52: 10060

• 187 Allingham MT, Bennett EL, Davies DH, Harper PM, Howard-Jones A, Mehdar YTH, Murphy PJ, Thomas DA, Caulkett PWR, Potter D, Lam CM, OʼDonoghue AC. Tetrahedron 2016; 72: 496