2.8 Metal-Catalyzed (5 + 1), (5 + 2), and (5 + 2 + 1) Cycloadditions

Abstract

Metal-catalyzed (5 + n) cycloaddition is a powerful strategy for the synthesis of six-, seven-, and eight-membered carbocycles and heterocycles. These cycloadditions usually involve oxidative cyclization to a metallacycle; insertion into the C—M bond (e.g., by carbon monoxide, an alkene, alkyne, or allene, or a combination thereof); and reductive elimination. Vinylcyclopropanes and 3-acyloxy-1,4-enynes are the most common five-carbon synthons. Recent advances in transition-metal-catalyzed (5 + 1), (5 + 2), and (5 + 2 + 1) cycloadditions including their development, mechanistic studies, and applications are reviewed in this chapter.

Schlüsselwörter

cycloaddition - transition metals - catalysis - vinylcyclopropanes - propargylic esters - (5 + 1) cycloaddition - (5 + 2) cycloaddition - (5 + 2 + 1) cycloaddition - carbocycles - heterocycles - seven-membered rings - alkenes - alkynes - allenes - imines - cyclopropanes - epoxides - rhodium - ruthenium - nickel - iron - dictamnol - aphanamol - allocyathin B2 - tremulenediol A - tremulenolide A - pseudolaric acid B - frondosin A - rameswaralide - hirsutene - desoxyhypnophilin - asteriscanolide

• 1 Lautens M, Klute W, Tam W. Chem. Rev. 1996; 96: 49

• 2 Ojima I, Tzamarioudaki M, Li ZY, Donovan RJ. Chem. Rev. 1996; 96: 635

• 3 Frühauf H.-W. Chem. Rev. 1997; 97: 523

• 4 Trost BM, Krische MJ. Synlett 1998; 1

• 5 Yet L. Chem. Rev. 2000; 100: 2963

• 6 Aubert C, Buisine O, Malacria M. Chem. Rev. 2002; 102: 813

• 7 Modern Rhodium-Catalyzed Organic Reactions. Evans PA. Wiley-VCH; Weinheim, Germany 2005

• 8 Michelet V, Toullec PY, Genêt J.-P. Angew. Chem. Int. Ed. 2008; 47: 4268

• 9 Yu Z.-X, Wang Y, Wang Y. Chem.–Asian J. 2010; 5: 1072

• 10 Inglesby PA, Evans PA. Chem. Soc. Rev. 2010; 39: 2791

• 11 Aubert C, Fensterbank L, Garcia P, Malacria M, Simonneau A. Chem. Rev. 2011; 111: 1954

• 12 Battiste MA, Pelphrey PM, Wright DL. Chem.–Eur. J. 2006; 12: 3438

• 13 Butenschön H. Angew. Chem. Int. Ed. 2008; 47: 5287

• 14 Nguyen TV, Hartmann JM, Enders D. Synthesis 2013; 45: 845

• 15 Ben-Shoshan R, Sarel S. J. Chem. Soc. D 1969; 883

• 16 Sarel S. Acc. Chem. Res. 1978; 11: 204

• 17 Aumann R. J. Am. Chem. Soc. 1974; 96: 2631

• 18 Taber DF, Kanai K, Jiang Q, Bui G. J. Am. Chem. Soc. 2000; 122: 6807

• 19 Semmelhack MF, Ho S, Steigerwald M, Lee MC. J. Am. Chem. Soc. 1987; 109: 4397

• 20 Iwasawa N, Owada Y, Matsuo T. Chem. Lett. 1995; 24: 115

• 21 Kurahashi T, de Meijere A. Synlett 2005; 2619

• 22 Murakami M, Itami K, Ubukata M, Tsuji I, Ito Y. J. Org. Chem. 1998; 63: 4

• 23 Kamitani A, Chatani N, Morimoto T, Murai S. J. Org. Chem. 2000; 65: 9230

• 24 Cho SH, Liebeskind LS. J. Org. Chem. 1987; 52: 2631

• 25 Brancour C, Fukuyama T, Ohta Y, Ryu I, Dhimane A.-L, Fensterbank L, Malacria M. Chem. Commun. (Cambridge) 2010; 46: 5470

• 26 Fukuyama T, Ohta Y, Brancour C, Miyagawa K, Ryu I, Dhimane A.-L, Fensterbank L, Malacria M. Chem.–Eur. J. 2012; 18: 7243

• 27 Rautenstrauch V. J. Org. Chem. 1984; 49: 950

• 28 Marion N, Nolan SP. Angew. Chem. Int. Ed. 2007; 46: 2750

• 29 Marco-Contelles J, Soriano E. Chem.–Eur. J. 2007; 13: 1350

• 30 Rudolph M, Hashmi ASK. Chem. Soc. Rev. 2012; 41: 2448

• 31 Shu X.-Z, Shu D, Schienebeck CM, Tang W. Chem. Soc. Rev. 2012; 41: 7698

• 32 Shu D, Li X, Zhang M, Robichaux PJ, Tang W. Angew. Chem. Int. Ed. 2011; 50: 1346

• 33 Shu D, Li X, Zhang M, Robichaux PJ, Guzei IA, Tang W. J. Org. Chem. 2012; 77: 6463

• 34 Jiang G.-J, Fu X.-F, Li Q, Yu Z.-X. Org. Lett. 2012; 14: 692

• 35 Taber DF, Bui G, Chen B. J. Org. Chem. 2001; 66: 3423

• 36 Singh V, Krishna UM, Vikrant , Trivedi GK. Tetrahedron 2008; 64: 3405

• 37 Pellissier H. Adv. Synth. Catal. 2011; 353: 189

• 38 Ylijoki KEO, Stryker JM. Chem. Rev. 2013; 113: 2244

• 39 Fraga BM. Nat. Prod. Rep. 2012; 29: 1334

• 40 Fraga BM. Nat. Prod. Rep. 2013; 30: 1226

• 41 Wender PA, Takahashi H, Witulski B. J. Am. Chem. Soc. 1995; 117: 4720

• 42 Wender PA, Dyckman AJ, Husfeld CO, Kadereit D, Love JA, Rieck H. J. Am. Chem. Soc. 1999; 121: 10442

• 43 Wender PA, Husfeld CO, Langkopf E, Love JA. J. Am. Chem. Soc. 1998; 120: 1940

• 44 Wender PA, Glorius F, Husfeld CO, Langkopf E, Love JA. J. Am. Chem. Soc. 1999; 121: 5348

• 45 Wender PA, Husfeld CO, Langkopf E, Love JA, Pleuss N. Tetrahedron 1998; 54: 7203

• 46 Wender PA, Haustedt LO, Lim J, Love JA, Williams TJ, Yoon J.-Y. J. Am. Chem. Soc. 2006; 128: 6302

• 47 Shintani R, Nakatsu H, Takatsu K, Hayashi T. Chem.–Eur. J. 2009; 15: 8692

• 48 Binger P, Wedemann P, Kozhushkov SI, de Meijere A. Eur. J. Org. Chem. 1998; 113

• 49 Wender PA, Rieck H, Fuji M. J. Am. Chem. Soc. 1998; 120: 10976

• 50 Wender PA, Barzilay CM, Dyckman AJ. J. Am. Chem. Soc. 2001; 123: 179

• 51 Wender PA, Gamber GG, Scanio MJC. Angew. Chem. Int. Ed. 2001; 40: 3895

• 52 Wender PA, Stemmler RT, Sirois LE. J. Am. Chem. Soc. 2010; 132: 2532

• 53 Wender PA, Fournogerakis DN, Jeffreys MS, Quiroz RV, Inagaki F, Pfaffenbach M. Nat. Chem. 2014; 6: 448

• 54 Wegner HA, de Meijere A, Wender PA. J. Am. Chem. Soc. 2005; 127: 6530

• 55 Jiao L, Ye S, Yu Z.-X. J. Am. Chem. Soc. 2008; 130: 7178

• 56 Li Q, Jiang G.-J, Jiao L, Yu Z.-X. Org. Lett. 2010; 12: 1332

• 57 Inagaki F, Sugikubo K, Miyashita Y, Mukai C. Angew. Chem. Int. Ed. 2010; 49: 2206

• 58 Wender PA, Pedersen TM, Scanio MJC. J. Am. Chem. Soc. 2002; 124: 15154

• 59 Feng J.-J, Zhang J. J. Am. Chem. Soc. 2011; 133: 7304

• 60 Shu X.-Z, Huang S, Shu D, Guzei IA, Tang W. Angew. Chem. Int. Ed. 2011; 50: 8153

• 61 Shu X.-Z, Li X, Shu D, Huang S, Schienebeck CM, Zhou X, Robichaux PJ, Tang W. J. Am. Chem. Soc. 2012; 134: 5211

• 62 Schienebeck CM, Robichaux PJ, Li X, Chen L, Tang W. Chem. Commun. (Cambridge) 2013; 49: 2616

• 63 Shu X.-Z, Schienebeck CM, Song W, Guzei IA, Tang W. Angew. Chem. Int. Ed. 2013; 52: 13601

• 64 Yu Z.-X, Wender PA, Houk KN. J. Am. Chem. Soc. 2004; 126: 9154

• 65 Yu Z.-X, Cheong PH.-Y, Liu P, Legault CY, Wender PA, Houk KN. J. Am. Chem. Soc. 2008; 130: 2378

• 66 Liu P, Cheong PH.-Y, Yu Z.-X, Wender PA, Houk KN. Angew. Chem. Int. Ed. 2008; 47: 3939

• 67 Liu P, Sirois LE, Cheong PH.-Y, Yu Z.-X, Hartung IV, Rieck H, Wender PA, Houk KN. J. Am. Chem. Soc. 2010; 132: 10127

• 68 Xu X, Liu P, Lesser A, Sirois LE, Wender PA, Houk KN. J. Am. Chem. Soc. 2012; 134: 11012

• 69 Hong X, Liu P, Houk KN. J. Am. Chem. Soc. 2013; 135: 1456

• 70 Hong X, Trost BM, Houk KN. J. Am. Chem. Soc. 2013; 135: 6588

• 71 Xu X, Liu P, Shu X.-Z, Tang W, Houk KN. J. Am. Chem. Soc. 2013; 135: 9271

• 72 Trost BM, Toste FD, Shen H. J. Am. Chem. Soc. 2000; 122: 2379

• 73 Trost BM, Shen HC. Angew. Chem. Int. Ed. 2001; 40: 2313

• 74 Trost BM, Shen HC, Horne DB, Toste FD, Steinmetz BG, Koradin C. Chem.–Eur. J. 2005; 11: 2577

• 75 Zuo G, Louie J. J. Am. Chem. Soc. 2005; 127: 5798

• 76 Fürstner A, Majima K, Martín R, Krause H, Kattnig E, Goddard R, Lehmann CW. J. Am. Chem. Soc. 2008; 130: 1992

• 77 Wender PA, Fuji M, Husfeld CO, Love JA. Org. Lett. 1999; 1: 137

• 78 Wender PA, Zhang L. Org. Lett. 2000; 2: 2323

• 79 Wender PA, Bi FC, Brodney MA, Gosselin F. Org. Lett. 2001; 3: 2105

• 80 Ashfeld BL, Martin SF. Org. Lett. 2005; 7: 4535

• 81 Ashfeld BL, Martin SF. Tetrahedron 2006; 62: 10497

• 82 Trost BM, Hu Y, Horne DB. J. Am. Chem. Soc. 2007; 129: 11781

• 83 Trost BM, Waser J, Meyer A. J. Am. Chem. Soc. 2007; 129: 14 556

• 84 Trost BM, Waser J, Meyer A. J. Am. Chem. Soc. 2008; 130: 16424

• 85 Jiao L, Yuan C, Yu Z.-X. J. Am. Chem. Soc. 2008; 130: 4421

• 86 Trost BM, Nguyen HM, Koradin C. Tetrahedron Lett. 2010; 51: 6232

• 87 Wender PA, Gamber GG, Hubbard RD, Zhang L. J. Am. Chem. Soc. 2002; 124: 2876

• 88 Wang Y, Wang J, Su J, Huang F, Jiao L, Liang Y, Yang D, Zhang S, Wender PA, Yu Z.-X. J. Am. Chem. Soc. 2007; 129: 10060

• 89 Liang Y, Jiang X, Yu Z.-X. Chem. Commun. (Cambridge) 2011; 47: 6659