2.3 Pauson–Khand Reactions

G. Dominguez; J. Pérez Castells

Abstract

The Pauson–Khand (2 + 2 + 1) cycloaddition (PKR) is one of the best ways to construct a cyclopentenone. In this review, standard procedures to perform both stoichiometric and catalytic Pauson–Khand reactions are presented. These include the use of homo- and heterogeneous catalysts as well as different promoters. Asymmetric versions are described, as are cascade processes where the Pauson–Khand reaction is combined with other transformations. The chapter ends with a summary of representative total syntheses of natural products where a Pauson–Khand reaction is used as the key step.

Key words

Pauson–Khand - cycloaddition - transition-metal catalysis - stereoselectivity - asymmetric synthesis - cobalt - rhodium - iridium - heterogeneous catalysis - cascade synthesis - total synthesis

• 1 The Pauson–Khand Reaction: Scope, Variations and Applications. Torres RR. Wiley; Hoboken, NJ 2012

• 2 Omae I. Coord. Chem. Rev. 2011; 255: 139

• 3 Strübing D, Beller M. Top. Organomet. Chem. 2006; 18: 165

• 4 Blanco-Urgoiti J, Añorbe L, Pérez-Serrano L, Domínguez G, Pérez-Castells J. Chem. Soc. Rev. 2004; 33: 32

• 5 Khand IU, Knox GR, Pauson PL, Watts WE. J. Chem. Soc. D 1971; 36

• 6 Park JH, Chang K.-M, Chung YK. Coord. Chem. Rev. 2009; 253: 2461

• 7 Schore NE, Croudace MC. J. Org. Chem. 1981; 46: 5436

• 8 Robert F, Milet A, Gimbert Y, Konya D, Greene AE. J. Am. Chem. Soc. 2001; 123: 5396

• 9 Fager-Jokela E, Muuronen M, Patzschke M, Helaja J. J. Org. Chem. 2012; 77: 9134

• 10 Moulton BE, Whitwood AC, Duhme-Klair AK, Lynam JM, Fairlamb IJS. J. Org. Chem. 2011; 76: 5320

• 11 Aiguabella N, del Pozo C, Verdaguer X, Fustero S, Riera A. Angew. Chem. 2013; 125: 5463 Angew. Chem. Int. Ed. 2013; 52: 5355

• 12 Krafft ME, Scott IL, Romero RH, Feibelmann S, Van Pelt CE. J. Am. Chem. Soc. 1993; 115: 7199

• 13 Kędzia JL, Kerr WJ, McPherson AR. Synlett 2010; 649

• 14 Smit WA, Kireev SL, Nefedov OM, Tarasov VA. Tetrahedron Lett. 1989; 30: 4021

• 15 Shambayati S, Crowe WE, Schreiber SL. Tetrahedron Lett. 1990; 31: 5289

• 16 Jeong N, Chung YK, Lee BY, Lee SH, Yoo S.-E. Synlett 1991; 204

• 17 Ford JG, Kerr WJ, Kirk GG, Lindsay DM, Middlemiss D. Synlett 2000; 1415

• 18 Pérez-Serrano L, Casarrubios L, Domínguez G, Pérez-Castells J. Org. Lett. 1999; 1: 1187

• 19 Marchueta I, Verdaguer X, Moyano A, Pericàs MA, Riera A. Org. Lett. 2001; 3: 3193

• 20 Krafft ME, Wright JA, Boñaga LVR. Tetrahedron Lett. 2003; 44: 3417

• 21 Perez del Valle C, Milet A, Gimbert Y, Greene AE. Angew. Chem. 2005; 117: 5863 Angew. Chem. Int. Ed. 2005; 44: 5717

• 22 Billington DC, Helps IM, Pauson PL, Thomson W, Willison D. J. Organomet. Chem. 1988; 354: 233

• 23 Krafft ME, Boñaga LVR, Hirosawa C. J. Org. Chem. 2001; 66: 3004

• 24 Sugihara T, Yamada M, Yamaguchi M, Nishizawa M. Synlett 1999; 771

• 25 Brown JA, Irvine S, Kerr WJ, Pearson CM. Org. Biomol. Chem. 2005; 3: 2396

• 26 Fischer S, Groth U, Jung M, Schneider A. Synlett 2002; 2023

• 27 Lagunas A, Mairata i Payeras A, Jimeno C, Pericàs MA. Org. Lett. 2005; 7: 3033

• 28 Asano K, Uesugi Y, Yoshida J.-I. Org. Lett. 2013; 15: 2398

• 29 Adrio J, Rodríguez Rivero M, Carretero JC. Org. Lett. 2005; 7: 431

• 30 Brummond KM, Mitasev B. Org. Lett. 2004; 6: 2245

• 31 Cao H, Van Ornum SG, Deschamps J, Flippen-Anderson J, Laib F, Cook JM. J. Am. Chem. Soc. 2005; 127: 933

• 32 de Meijere A, Becker H, Stolle A, Kozhushkov SI, Bes MT, Salaün J, Noltemeyer M. Chem.–Eur. J. 2005; 11: 2471

• 33 de Bruin TJM, Milet A, Greene AE, Gimbert Y. J. Org. Chem. 2004; 69: 1075

• 34 Lledó A, Fuster A, Revés M, Verdaguer X, Riera A. Chem. Commun. (Cambridge) 2013; 49: 3055

• 35 Kizirian J.-C, Aiguabella N, Pesquer A, Fustero S, Bello P, Verdaguer X, Riera A. Org. Lett. 2010; 12: 5620

• 36 Aiguabella N, Pesquer A, Verdaguer X, Riera A. Org. Lett. 2013; 15: 2696

• 37 Revés M, Lledó A, Ji Y, Blasi E, Riera A, Verdaguer X. Org. Lett. 2012; 14: 3534

• 38 Pallerla MK, Yap GPA, Fox JM. J. Org. Chem. 2008; 73: 6137

• 39 Gibson SE, Mainolfi N, Kalindjian SB, Wright PT. Angew. Chem. 2004; 116: 5798 Angew. Chem. Int. Ed. 2004; 43: 5680

• 40 Seigal BA, An MH, Snapper ML. Angew. Chem. 2005; 117: 5009 Angew. Chem. Int. Ed. 2005; 44: 4929

• 41 Schore NE. Org. React. (N. Y.) 1991; 40: 1

• 42 Billington DC, Bladon P, Helps IM, Pauson PL, Thomson W, Willison D. J. Chem. Res., Miniprint 1988; 2601

• 43 Jeong N, Hwang SH. Angew. Chem. 2000; 112: 650 Angew. Chem. Int. Ed. 2000; 39: 636

• 44 Vázquez-Romero A, Cárdenas L, Blasi E, Verdaguer X, Riera A. Org. Lett. 2009; 11: 3104

• 45 Kerr WJ, McLaughlin M, Pauson PL, Robertson SM. Chem. Commun. (Cambridge) 1999; 2171

• 46 Pérez-Serrano L, Blanco-Urgoiti J, Casarrubios L, Domínguez G, Pérez-Castells J. J. Org. Chem. 2000; 65: 3513

• 47 Kitagaki S, Inagaki F, Mukai C. Chem. Soc. Rev. 2014; 43: 2956

• 48 Ahmar M, Locatelli C, Colombier D, Cazes B. Tetrahedron Lett. 1997; 38: 5281

• 49 Pagenkopf BL, Belanger DB, OʼMahony DJR, Livinghouse T. Synthesis 2000; 1009

• 50 Brummond KM, Wan H, Kent JL. J. Org. Chem. 1998; 63: 6535

• 51 Brummond KM, Lu J, Petersen J. J. Am. Chem. Soc. 2000; 122: 4915

• 52 Pérez-Serrano L, Casarrubios L, Domínguez G, Pérez-Castells J. Chem. Commun. (Cambridge) 2001; 2602

• 53 Mukai C, Nomura I, Kitagaki S. J. Org. Chem. 2003; 68: 1376

• 54 Magnus P, Exon C, Albaugh-Robertson P. Tetrahedron Lett. 1985; 26: 5861

• 55 Pericàs MA, Balsells J, Castro J, Marchueta I, Moyano A, Riera A, Vázquez J, Verdaguer X. Pure Appl. Chem. 2002; 74: 167

• 56 Banide EV, Müller-Bunz H, Manning AR, Evans P, McGlinchey MJ. Angew. Chem. 2007; 119: 2965 Angew. Chem. Int. Ed. 2007; 46: 2907

• 57 Lesage D, Milet A, Memboeuf A, Blu J, Greene AE, Tabet J.-C, Gimbert Y. Angew. Chem. 2014; 126: 1970 Angew. Chem. Int. Ed. 2014; 53: 1939

• 58 Yamanaka M, Nakamura E. J. Am. Chem. Soc. 2001; 123: 1703

• 59 de Bruin TJM, Milet A, Robert F, Gimbert Y, Greene AE. J. Am. Chem. Soc. 2001; 123: 7184

• 60 Schulte JH, Gleiter R, Rominger F. Org. Lett. 2002; 4: 3301

• 61 Cabot R, Lledó A, Revés M, Riera A, Verdaguer X. Organometallics 2007; 26: 1134

• 62 Rautenstrauch V, Mégard P, Conesa J, Küster W. Angew. Chem. 1990; 102: 1441 Angew. Chem. Int. Ed. Engl. 1990; 29: 1413

• 63 Shibata T. Adv. Synth. Catal. 2006; 348: 2328

• 64 Jeong N, Hwang SH, Lee Y, Chung YK. J. Am. Chem. Soc. 1994; 116: 3159

• 65 Comely AC, Gibson SE, Stevenazzi A, Hales NJ. Tetrahedron Lett. 2001; 42: 1183

• 66 Hayashi M, Hashimoto Y, Yamamoto Y, Usuki J, Saigo K. Angew. Chem. 2000; 112: 645 Angew. Chem. Int. Ed. 2000; 39: 631

• 67 Tang Y, Deng L, Zhang Y, Dong G, Chen J, Yang Z. Org. Lett. 2005; 7: 593

• 68 Wang Y, Xu L, Yu R, Chen J, Yang Z. Chem. Commun. (Cambridge) 2012; 48: 8183

• 69 Sugihara T, Yamaguchi M. Synlett 1998; 1384

• 70 Blanco-Urgoiti J, Casarrubios L, Domínguez G, Pérez-Castells J. Tetrahedron Lett. 2002; 43: 5763

• 71 Dahan A, Portnoy M. Chem. Commun. (Cambridge) 2002; 2700

• 72 Pagenkopf BL, Livinghouse T. J. Am. Chem. Soc. 1996; 118: 2285

• 73 Belanger DB, Livinghouse T. Tetrahedron Lett. 1998; 39: 7641

• 74 Krafft ME, Boñaga LVR, Hirosawa C. Tetrahedron Lett. 1999; 40: 9177

• 75 Sugihara T, Yamaguchi M. J. Am. Chem. Soc. 1998; 120: 10782

• 76 Boñaga LVR, Wright JA, Krafft ME. Chem. Commun. (Cambridge) 2004; 1746

• 77 Kobayashi T, Koga Y, Narasaka K. J. Organomet. Chem. 2001; 624: 73

• 78 Jeong N, Sung BK, Kim JS, Park SB, Seo SD, Shin JY, In KY, Choi YK. Pure Appl. Chem. 2002; 74: 85

• 79 Wang H, Sawyer JR, Evans PA, Baik M.-H. Angew. Chem. 2008; 120: 348 Angew. Chem. Int. Ed. 2008; 47: 342

• 80 Baik M.-H, Mazumder S, Ricci P, Sawyer JR, Song Y.-G, Wang H, Evans PA. J. Am. Chem. Soc. 2011; 133: 7621

• 81 Jeong N, Sung BK, Choi YK. J. Am. Chem. Soc. 2000; 122: 6771

• 82 Kim DE, Ratovelomanana-Vidal V, Jeong N. Adv. Synth. Catal. 2010; 352: 2032

• 83 Kim DE, Kim IS, Ratovelomanana-Vidal V, Genêt J.-P, Jeong N. J. Org. Chem. 2008; 73: 7985

• 84 Fan B.-M, Xie J.-H, Li S, Tu Y.-Q, Zhou Q.-L. Adv. Synth. Catal. 2005; 347: 759

• 85 Kim DE, Choi C, Kim IS, Jeulin S, Ratovelomanana-Vidal V, Genêt J.-P, Jeong N. Adv. Synth. Catal. 2007; 349: 1999

• 86 Croatt MP, Wender PA. Eur. J. Org. Chem. 2010; 19

• 87 Wender PA, Deschamps NM, Gamber GG. Angew. Chem. 2003; 115: 1897 Angew. Chem. Int. Ed. 2003; 42: 1853

• 88 Wender PA, Deschamps NM, Williams TJ. Angew. Chem. 2004; 116: 3138 Angew. Chem. Int. Ed. 2004; 43: 3076

• 89 Pitcock Jr. WH, Lord RL, Baik M.-H. J. Am. Chem. Soc. 2008; 130: 5821

• 90 Mukai C, Nomura I, Yamanishi K, Hanaoka M. Org. Lett. 2002; 4: 1755

• 91 Brummond KM, Chen H, Fisher KD, Kerekes AD, Rickards B, Sill PC, Geib SJ. Org. Lett. 2002; 4: 1931

• 92 Morimoto T, Fuji K, Tsutsumi K, Kakiuchi K. J. Am. Chem. Soc. 2002; 124: 3806

• 93 Shibata T, Toshida N, Takagi K. Org. Lett. 2002; 4: 1619

• 94 Shibata T, Toshida N, Takagi K. J. Org. Chem. 2002; 67: 7446

• 95 Fuji K, Morimoto T, Tsutsumi K, Kakiuchi K. Angew. Chem. 2003; 115: 2511 Angew. Chem. Int. Ed. 2003; 42: 2409

• 96 Fuji K, Morimoto T, Tsutsumi K, Kakiuchi K. Tetrahedron Lett. 2004; 45: 9163

• 97 Kwong FY, Lee HW, Qiu L, Lam WH, Li Y.-M, Kwong HL, Chan ASC. Adv. Synth. Catal. 2005; 347: 1750

• 98 Park JH, Cho Y, Chung YK. Angew. Chem. 2010; 122: 5264 Angew. Chem. Int. Ed. 2010; 49: 5138

• 99 Shibata T, Takagi K. J. Am. Chem. Soc. 2000; 122: 9852

• 100 Shibata T, Toshida N, Yamasaki M, Maekawa S, Takagi K. Tetrahedron 2005; 61: 9974

• 101 Lu Z.-L, Neumann E, Pfaltz A. Eur. J. Org. Chem. 2007; 4189

• 102 Jeong N, Kim DH, Choi JH. Chem. Commun. (Cambridge) 2004; 1134

• 103 Hicks FA, Kablaoui NM, Buchwald SL. J. Am. Chem. Soc. 1999; 121: 5881

• 104 Hicks FA, Buchwald SL. J. Am. Chem. Soc. 1999; 121: 7026

• 105 Sturla SJ, Buchwald SL. Organometallics 2002; 21: 739

• 106 Morimoto T, Chatani N, Fukumoto Y, Murai S. J. Org. Chem. 1997; 62: 3762

• 107 Kondo T, Suzuki N, Okada T, Mitsudo T.-A. J. Am. Chem. Soc. 1997; 119: 6187

• 108 Itami K, Mitsudo K, Yoshida J.-I. Angew. Chem. 2002; 114: 3631 Angew. Chem. Int. Ed. 2002; 41: 3481

• 109 Paolillo R, Gallo V, Mastrorilli P, Nobile CF, Rosé J, Braunstein P. Organometallics 2008; 27: 741

• 110 Tang Y, Deng L, Zhang Y, Dong G, Chen J, Yang Z. Org. Lett. 2005; 7: 1657

• 111 Wu N, Deng L, Liu L, Liu Q, Li C, Yang Z. Chem.–Asian J. 2013; 8: 65

• 112 Lan Y, Deng L, Liu J, Wang C, Wiest O, Yang Z, Wu Y.-D. J. Org. Chem. 2009; 74: 5049

• 113 Kim S.-W, Son SU, Lee SI, Hyeon T, Chung YK. J. Am. Chem. Soc. 2000; 122: 1550

• 114 Kim S.-W, Son SU, Lee SS, Hyeon T, Chung YK. Chem. Commun. (Cambridge) 2001; 2212

• 115 Park KH, Son SU, Chung YK. Tetrahedron Lett. 2003; 44: 2827

• 116 Son SU, Park KH, Chung YK. Org. Lett. 2002; 4: 3983

• 117 Muller J.-L, Klankermayer J, Leitner W. Chem. Commun. (Cambridge) 2007; 1939

• 118 Park KH, Son SU, Chung YK. Chem. Commun. (Cambridge) 2003; 1898

• 119 Park JH, Chung YK. Dalton Trans. 2008; 2369

• 120 Park KH, Chung YK. Adv. Synth. Catal. 2005; 347: 854

• 121 Muller J.-L, Rickers A, Leitner W. Adv. Synth. Catal. 2007; 349: 287

• 122 Goettmann F, Thomas A, Antonietti M. Angew. Chem. 2007; 119: 2773 Angew. Chem. Int. Ed. 2007; 46: 2717

• 123 The Pauson–Khand Reaction: Scope, Variations and Applications Torres RR. Wiley Hoboken, NJ 2012; 69–167

• 124 Brummond KM, Curran DP, Mitasev B, Fischer S. J. Org. Chem. 2005; 70: 1745

• 125 Ghosh SK, Hsung RP, Liu J. J. Am. Chem. Soc. 2005; 127: 8260

• 126 McCormack MP, Waters SP. J. Org. Chem. 2013; 78: 1176

• 127 Brummond KM, Curran DP, Mitasev B, Fischer S. J. Org. Chem. 2005; 70: 1745

• 128 Grillet F, Brummond KM. J. Org. Chem. 2013; 78: 3737

• 129 Poch M, Valentí E, Moyano A, Pericàs MA, Castro J, DeNicola A, Greene AE. Tetrahedron Lett. 1990; 31: 7505

• 130 Castro J, Sörensen H, Riera A, Morin C, Moyano A, Pericàs MA, Greene AE. J. Am. Chem. Soc. 1990; 112: 9388

• 131 Castro J, Moyano A, Pericàs MA, Riera A, Greene AE, Alvarez-Larena A, Piniella JF. J. Org. Chem. 1996; 61: 9016

• 132 Bernardes V, Verdaguer X, Kardos N, Riera A, Moyano A, Pericàs MA, Greene AE. Tetrahedron Lett. 1994; 35: 575

• 133 Verdaguer X, Moyano A, Pericàs MA, Riera A, Greene AE, Piniella JF, Alvarez-Larena A. J. Organomet. Chem. 1992; 433: 305

• 134 Tormo J, Verdaguer X, Moyano A, Pericàs MA, Riera A. Tetrahedron 1996; 52: 14021

• 135 Verdaguer X, Vázquez J, Fuster G, Bernardes-Génisson V, Greene AE, Moyano A, Pericàs MA, Riera A. J. Org. Chem. 1998; 63: 7037

• 136 Fonquerna S, Rios R, Moyano A, Pericàs MA, Riera A. Eur. J. Org. Chem. 1999; 3459

• 137 Fonquerna S, Moyano A, Pericàs MA, Riera A. J. Am. Chem. Soc. 1997; 119: 10225

• 138 Adrio J, Carretero JC. J. Am. Chem. Soc. 1999; 121: 7411

• 139 Rodríguez Rivero M, de la Rosa JC, Carretero JC. J. Am. Chem. Soc. 2003; 125: 14992

• 140 Garcia Ruano JL, Torrente E, Parra A, Alemán J, Martín-Castro AM. J. Org. Chem. 2012; 77: 6583

• 141 Verdaguer X, Lledó A, López-Mosquera C, Maestro MA, Pericàs MA, Riera A. J. Org. Chem. 2004; 69: 8053

• 142 Solà J, Riera A, Verdaguer X, Maestro MA. J. Am. Chem. Soc. 2005; 127: 13629

• 143 Lledó A, Solà J, Verdaguer X, Riera A, Maestro MA. Adv. Synth. Catal. 2007; 349: 2121

• 144 Kim DE, Kwak J, Kim IS, Jeong N. Adv. Synth. Catal. 2009; 351: 97

• 145 Sturla SJ, Buchwald SL. J. Org. Chem. 2002; 67: 3398

• 146 Gibson SE, Hardick DJ, Haycock PR, Kaufmann KAC, Miyazaki A, Tozer MJ, White AJP. Chem.–Eur. J. 2007; 13: 7099

• 147 Fjermestad T, Pericàs MA, Maseras F. J. Mol. Catal. A: Chem. 2010; 324: 127

• 148 Fjermestad T, Pericàs MA, Maseras F. Chem.–Eur. J. 2011; 17: 10050

• 149 Pérez-Castells J. Top. Organomet. Chem. 2006; 19: 207

• 150 Finnegan DF, Snapper ML. J. Org. Chem. 2011; 76: 3644

• 151 Díaz D, Betancort JM, Martín VS. Synlett 2007; 343

• 152 Smit WA, Gybin AS, Shashkov AS, Struchkov YT, Kyzʼmina LG, Mikaelian GS, Caple R, Swanson ED. Tetrahedron Lett. 1986; 27: 1241

• 153 Jamison TF, Shambayati S, Crowe WE, Schreiber SL. J. Am. Chem. Soc. 1997; 119: 4353

• 154 Closser KD, Quintal MM, Shea KM. J. Org. Chem. 2009; 74: 3680

• 155 Evans PA, Robinson JE. J. Am. Chem. Soc. 2001; 123: 4609

• 156 Son SU, Park KH, Chung YK. J. Am. Chem. Soc. 2002; 124: 6838

• 157 Kim DH, Chung YK. Chem. Commun. (Cambridge) 2005; 1634

• 158 Chen W, Tay J.-H, Ying J, Yu X.-Q, Pu L. J. Org. Chem. 2013; 78: 2256

• 159 Odedra A, Wu C.-J, Madhushaw RJ, Wang S.-L, Liu R.-S. J. Am. Chem. Soc. 2003; 125: 9610

• 160 van der Waals A, Keese R. J. Chem. Soc., Chem. Commun. 1992; 570

• 161 Cao H, Mundla SR, Cook JM. Tetrahedron Lett. 2003; 44: 6165

• 162 Chen G.-Q, Shi M. Chem. Commun. (Cambridge) 2013; 49: 698

• 163 Boñaga LVR, Krafft ME. Tetrahedron 2004; 60: 9795

• 164 Krafft ME, Boñaga LVR, Wright JA, Hirosawa C. J. Org. Chem. 2002; 67: 1233

• 165 Pérez-Serrano L, Domínguez G, Pérez-Castells J. J. Org. Chem. 2004; 69: 5413

• 166 Chatani N, Morimoto T, Fukumoto Y, Murai S. J. Am. Chem. Soc. 1998; 120: 5335

• 167 Adrio J, Carretero JC. J. Am. Chem. Soc. 2007; 129: 778

• 168 Chatani N, Morimoto T, Kamitani A, Fukumoto Y, Murai S. J. Organomet. Chem. 1999; 579: 177

• 169 Saito T, Sugizaki K, Otani T, Suyama T. Org. Lett. 2007; 9: 1239

• 170 Saito T, Shiotani M, Otani T, Hasaba S. Heterocycles 2003; 60: 1045

• 171 Aburano D, Yoshida T, Miyakoshi N, Mukai C. J. Org. Chem. 2007; 72: 6878

• 172 Saito T, Nihei H, Otani T, Suyama T, Furukawa N, Saito M. Chem. Commun. (Cambridge) 2008; 172

• 173 Saito T, Sugizaki K, Osada H, Kutsumura N, Otani T. Heterocycles 2010; 80: 207

• 174 Kondo T, Nomura M, Ura Y, Wada K, Mitsudo T.-A. J. Am. Chem. Soc. 2006; 128: 14816

• 175 Iwata T, Inagaki F, Mukai C. Angew. Chem. 2013; 125: 11344 Angew. Chem. Int. Ed. 2013; 52: 11138

• 176 Van Ornum SG, Hoerner S, Cook JM, The Pauson–Khand Reaction: Scope, Variations and Applications Torres RR. Wiley Hoboken, NJ 2012; 211–231

• 177 Pallerla MK, Fox JM. Org. Lett. 2007; 9: 5625

• 178 Farwick A, Helmchen G. Org. Lett. 2010; 12: 1108

• 179 Min S.-J, Danishefsky SJ. Angew. Chem. 2007; 119: 2249 Angew. Chem. Int. Ed. 2007; 46: 2199

• 180 Hirose T, Miyakoshi N, Mukai C. J. Org. Chem. 2008; 73: 1061

• 181 Inagaki F, Kinebuchi M, Miyakoshi N, Mukai C. Org. Lett. 2010; 12: 1800

• 182 McKerrall SJ, Jørgensen L, Kuttruff CA, Ungeheuer F, Baran PS. J. Am. Chem. Soc. 2014; 136: 5799

• 183 Huang J, Fang L, Long R, Shi L.-L, Shen H.-J, Li C.-C, Yang Z. Org. Lett. 2013; 15: 4018

• 184 Yang Y, Fu X, Chen J, Zhai H. Angew. Chem. 2012; 124: 9963 Angew. Chem. Int. Ed. 2012; 51: 9825

• 185 Fujioka K, Yokoe H, Yoshida M, Shishido K. Org. Lett. 2012; 14: 244

• 186 Nakayama A, Kogure N, Kitajima M, Takayama H. Angew. Chem. 2011; 123: 8175 Angew. Chem. Int. Ed. 2011; 50: 8025