2.4 1,3-Dipolar Cycloadditions Involving Carbonyl or Azomethine Ylides

Abstract

Carbonyl ylides, which behave as active 1,3-dipole species, have found numerous applications in organic synthesis, especially in the formation of five-membered heterocycles. Among the versatile transformations of carbonyl ylides, 1,3-dipolar cycloadditions with π-bonds, including (3 + 2)-cycloaddition reactions with carbon–carbon π-bonds, aldehydes, and imines, are ubiquitous and important reactions. This chapter focuses on recent advances in these catalytic (3 + 2)-cycloaddition reactions and the examples presented emphasize the chemo-, diastereo-, and enantiocontrol that can be achieved. Also described are selected examples of cycloaddition reactions with azomethine ylides, which behave with similar reactivity to carbonyl ylides, to give the corresponding N-heterocycles. In addition, some selected applications of these (3 + 2)-cycloaddition reactions in natural product synthesis are highlighted.

Key words

(3 + 2) cycloaddition - carbonyl ylides - azomethine ylides - 1,3-dipoles - diazo compounds - chiral dirhodium carboxylates - heterocycles - five-membered rings - natural product synthesis - asymmetric catalysis

• 1 Muthusamy S, Krishnamurthi J. Top. Heterocycl. Chem. 2008; 12: 147

• 2 Padwa A. Helv. Chim. Acta 2005; 88: 1357

• 3 Wang J, In Comprehensive Organometallic Chemistry III Crabtree RH, Mingos DMP. Elsevier Oxford 2007; Vol 11 159–163

• 4 Buchner E, Curtius T. Ber. Dtsch. Chem. Ges. 1885; 18: 2371

• 5 de March P, Huisgen R. J. Am. Chem. Soc. 1982; 104: 4952

• 6 Bentabed-Ababsa G, Hamza-Reguig S, Derdour A, Domingo LR, Sáez JA, Roisnel T, Dorcet V, Nassar E, Mongin F. Org. Biomol. Chem. 2012; 10: 8434

• 7 Elliott GI, Velcicky J, Ishikawa H, Li Y, Boger DL. Angew. Chem. 2006; 118: 636 Angew. Chem. Int. Ed. 2006; 45: 620

• 8 Bèkhazi M, Warkentin J. J. Am. Chem. Soc. 1983; 105: 1289

• 9 Sammakia T, Smith RS. J. Am. Chem. Soc. 1992; 114: 10998

• 10 Woodall EL, Simanis JA, Hamaker CG, Goodell JR, Mitchell TA. Org. Lett. 2013; 15: 3270

• 11 Kusama H, Funami H, Shido M, Hara Y, Takaya J, Iwasawa N. J. Am. Chem. Soc. 2005; 127: 2709

• 12 Doyle MP, Hu W, Timmons DJ. Org. Lett. 2001; 3: 933

• 13 DeAngelis A, Panne P, Yap GPA, Fox JM. J. Org. Chem. 2008; 73: 1435

• 14 Tsutsui H, Shimada N, Abe T, Anada M, Nakajima M, Nakamura S, Nambu H, Hashimoto S. Adv. Synth. Catal. 2007; 349: 521

• 15 Padwa A, Cheng B, Zou Y. Aust. J. Chem. 2014; 67: 343

• 16 Hodgson DM, Glen R, Redgrave AJ. Tetrahedron: Asymmetry 2009; 20: 754

• 17 Hodgson DM, Avery TD, Donohue AC. Org. Lett. 2002; 4: 1809

• 18 Zhou C.-Y, Yu W.-Y, Che C.-M. Org. Lett. 2002; 4: 3235

• 19 Rout L, Harned AM. Chem.–Eur. J. 2009; 15: 12926

• 20 Lu C.-D, Chen Z.-Y, Liu H, Hu W.-H, Mi A.-Q, Doyle MP. J. Org. Chem. 2004; 69: 4856

• 21 Hashimoto Y, Itoh K, Kakehi A, Shiro M, Suga H. J. Org. Chem. 2013; 78: 6182

• 22 Hodgson DM, Labande AH, Glen R, Redgrave AJ. Tetrahedron: Asymmetry 2003; 14: 921

• 23 Hodgson DM, Labande AH, Pierard FYTM, Expósito Castro MÁ.. J. Org. Chem. 2003; 68: 6153

• 24 Shimada N, Anada M, Nakamura S, Nambu H, Tsutsui H, Hashimoto S. Org. Lett. 2008; 10: 3603

• 25 Takeda K, Oohara T, Shimada N, Nambu H, Hashimoto S. Chem.–Eur. J. 2011; 17: 13992

• 26 Krishnamurthi J, Nambu H, Takeda K, Anada M, Yamano A, Hashimoto S. Org. Biomol. Chem. 2013; 11: 5374

• 27 Shimada N, Oohara T, Krishnamurthi J, Nambu H, Hashimoto S. Org. Lett. 2011; 13: 6284

• 28 Suga H, Ishimoto D, Higuchi S, Ohtsuka M, Arikawa T, Tsuchida T, Kakehi A, Baba T. Org. Lett. 2007; 9: 4359

• 29 Suga H, Hashimoto Y, Yasumura S, Takezawa R, Itoh K, Kakehi A. J. Org. Chem. 2013; 78: 10840

• 30 Hodgson DM, Stupple PA, Johnstone C. Tetrahedron Lett. 1997; 38: 6471

• 31 Davies HML, Bruzinski PR, Lake DH, Kong N, Fall MJ. J. Am. Chem. Soc. 1996; 118: 6897

• 32 Lu C.-D, Chen Z.-Y, Liu H, Hu W.-H, Mi A.-Q. Org. Lett. 2004; 6: 3071

• 33 Muthusamy S, Ramkumar R, Mishra AK. Tetrahedron Lett. 2011; 52: 148

• 34 Chen Z, Wei L, Zhang J. Org. Lett. 2011; 13: 1170

• 35 Suga H, Ebiura Y, Fukushima K, Kakehi A, Baba T. J. Org. Chem. 2005; 70: 10782

• 36 Torssell S, Kienle M, Somfai P. Angew. Chem. 2005; 117: 3156 Angew. Chem. Int. Ed. 2005; 44: 3096

• 37 Torssell S, Somfai P. Adv. Synth. Catal. 2006; 348: 2421

• 38 Gan Y, Harwood LM, Richards SC, Smith IED, Vinader V. Tetrahedron: Asymmetry 2009; 20: 723

• 39 Xu X, Guo X, Han X, Yang L, Hu W. Org. Chem. Front. 2014; 1: 181

• 40 Narayan R, Potowski M, Jia Z.-J, Antonchick AP, Waldmann H. Acc. Chem. Res. 2014; 47: 1296

• 41 Yu J, Shi F, Gong L.-Z. Acc. Chem. Res. 2011; 44: 1156

• 42 Randjelovic J, Simic M, Tasic G, Husinec S, Savic V. Curr. Org. Chem. 2014; 18: 1073

• 43 Tao H.-Y, Wang C.-J. Synlett 2014; 25: 461

• 44 Zhou C.-Y, Huang J.-S, Che C.-M. Synlett 2010; 2681

• 45 Doyle MP, Hu W, Timmons DJ. Org. Lett. 2001; 3: 3741

• 46 Doyle MP, Yan M, Hu W, Gronenberg LS. J. Am. Chem. Soc. 2003; 125: 4692

• 47 Yan M, Jacobsen N, Hu W, Gronenberg LS, Doyle MP, Colyer JT, Bykowski D. Angew. Chem. 2004; 116: 6881 Angew. Chem. Int. Ed. 2004; 43: 6713

• 48 Li G.-Y, Chen J, Yu W.-Y, Hong W, Che C.-M. Org. Lett. 2003; 5: 2153

• 49 Xu H.-W, Li G.-Y, Wong M.-K, Che C.-M. Org. Lett. 2005; 7: 5349

• 50 Galliford CV, Scheidt KA. J. Org. Chem. 2007; 72: 1811

• 51 Wang M.-Z, Xu H.-W, Liu Y, Wong M.-K, Che C.-M. Adv. Synth. Catal. 2006; 348: 2391

• 52 Geldenhuys WJ, Malan SF, Bloomquist JR, Marchand AP, Van der Schyf CJ. Med. Res. Rev. 2005; 25: 21

• 53 Padwa A. Tetrahedron 2011; 67: 8057

• 54 Mejía-Oneto JM, Padwa A. Helv. Chim. Acta 2008; 91: 285

• 55 Shimada N, Hanari T, Kurosaki Y, Takeda K, Anada M, Nambu H, Shiro M, Hashimoto S. J. Org. Chem. 2010; 75: 6039

• 56 Herbert RB, In The Chemistry of Heterocyclic Compounds. Saxton JE. Wiley; Chichester, UK 1994. Vol. 25. Part 4, Chapter 1.

• 57 Toyota M, Ihara M. Nat. Prod. Rep. 1998; 327