Asymmetric [3+2] Cycloaddition of Azomethine Ylides Catalyzed by Silver(I) Triflate with a Chiral Bipyrrolidine-Derived Phosphine Ligand

Abstract

Two novel chiral bipyrrolidine-derived phosphine ligands L1 and L2 were synthesized. The ‘AgOTf + L1’ protocol catalyzes the asymmetric [3+2] cycloaddition of azomethine ylides with alkenes to give highly substituted pyrrolidines in good yields (up to 90%) with moderate to high diastereoselectivities (up to >19:1 dr) and enantioselectivities (up to 76%).

Key words

asymmetric [3+2] cycloaddition - silver catalysis - azomethine ylides - chiral phosphine ligand - highly substituted pyrrolines

• References


Reviews:
• 1a Michael JP. Nat. Prod. Rep. 2008; 25: 139
• 1b Cheng Y, Huang Z.-T, Wang M.-X. Curr. Org. Chem. 2004; 8: 325
• 1c Enders D, Thiebes C. Pure Appl. Chem. 2001; 73: 573

Reviews:
• 2a Sulzer-Mossé S, Alexakis A. Chem. Commun. 2007; 3123
• 2b List B. Chem. Commun. 2006; 819
• 2c Guillena G, Ramón DJ. Tetrahedron: Asymmetry 2006; 17: 1465

Reviews:
• 3a Nájera C, Sansano JM. Org. Biomol. Chem. 2009; 7: 4567
• 3b Nair V, Suja TD. Tetrahedron 2007; 63: 12247
• 3c Coldham I, Hufton R. Chem. Rev. 2005; 105: 2765

Reviews on transition-metal-catalyzed asymmetric [3+2] cycloaddition of azomethine ylides with alkenes:
• 4a Adrio J, Carretero JC. Chem. Commun. 2011; 47: 6784
• 4b Nájera C, Sansano JM. Top. Heterocycl. Chem. 2008; 12: 117
• 4c Pandey G, Banerjee P, Gadre SR. Chem. Rev. 2006; 106: 4484
• 4d Nájera C, Sansano JM. Angew. Chem. Int. Ed. 2005; 44: 6272

Selected examples on transition-metal-catalyzed asymmetric [3+2] cycloaddition of azomethine ylides with alkenes:
• 5a Conde E, Bello D, de Cózar A, Sánchez M, Vázquez MA, Cossio FP. Chem. Sci. 2012; 3: 1486
• 5b Fukuzawa S.-i, Oki H. Org. Lett. 2008; 10: 1747
• 5c Wang C.-J, Liang G, Xue Z.-Y, Gao F. J. Am. Chem. Soc. 2008; 130: 17250
• 5d Yan X.-X, Peng Q, Zhang Y, Zhang K, Hong W, Hou X.-L, Wu Y.-D. Angew. Chem. Int. Ed. 2006; 45: 1979
• 5e Gothelf AS, Gothelf KV, Hazell RG, Jørgensen KA. Angew. Chem. Int. Ed. 2002; 41: 4236

Reviews on silver-catalyzed asymmetric [3+2] cycloaddition of azomethine ylides with alkenes:
• 6a Chen Q.-A, Wang D.-S, Zhou Y.-G. Chem. Commun. 2010; 46: 4043
• 6b Naodovic M, Yamamoto H. Chem. Rev. 2008; 108: 3132
• 6c Álvarez-Corral M, Muñoz-Dorado M, Rodríguez-García I. Chem. Rev. 2008; 108: 3174

Selected examples on silver-catalyzed asymmetric [3+2] cycloaddition of azomethine ylides with alkenes:
• 7a Xue Z.-Y, Liu T.-L, Lu Z, Huang H, Tao H.-Y, Wang C.-J. Chem. Commun. 2010; 46: 1727
• 7b Oura I, Shimizu K, Ogata K, Fukuzawa S.-i. Org. Lett. 2010; 12: 1752
• 7c Yamashita Y, Guo X.-X, Takashita R, Kobayashi S. J. Am. Chem. Soc. 2010; 132: 3262
• 7d Wang C.-J, Xue Z.-Y, Liang G, Lu Z. Chem. Commun. 2009; 2905
• 7e Zeng W, Chen G.-Y, Zhou Y.-G, Li Y.-X. J. Am. Chem. Soc. 2007; 129: 750
• 7f Chen C, Li X, Schreiber SL. J. Am. Chem. Soc. 2003; 125: 10174
• 7g Longmire JM, Wang B, Zhang X. J. Am. Chem. Soc. 2002; 124: 13400
• 8a Suzuki K, Oldenburg PD, Que Jr. L. Angew. Chem. Int. Ed. 2008; 47: 1887
• 8b Oishi T, Hirama M. J. Org. Chem. 1989; 54: 5834

Reviews:
• 9a Chen MS, White MC. Science (Washington, D.C.) 2010; 327: 566
• 9b Christmann M. Angew. Chem. Int. Ed. 2008; 47: 2740
• 9c Chen MS, White MC. Science (Washington, D.C.) 2007; 318: 783
• 10a Bigi MA, Reed SA, White MC. Nat. Chem. 2011; 3: 216
• 10b Vermeulen NA, Chen MS, White MC. Tetrahedron 2009; 65: 3078
• 11a Jia X, Lin A, Mao Z, Zhu C, Cheng Y. Molecules 2011; 16: 2971
• 11b Sulzer-Mossé S, Alexakis A, Mareda J, Bollot G, Bernardinelli G, Filinchuk Y. Chem.–Eur. J. 2009; 15: 3204
• 11c Zhu Q, Huang H, Shi D, Shen Z, Xia C. Org. Lett. 2009; 11: 4536
• 12a Wang J.-C, Xu Z.-J, Guo Z, Deng Q.-H, Zhou C.-Y, Wan X.-L, Che C.-M. Chem. Commun. 2012; 48: 4299
• 12b Chen G.-Q, Xu Z.-J, Liu Y, Zhou C.-Y, Che C.-M. Synlett 2011; 1174
• 12c Chen G.-Q, Xu Z.-J, Chan SL.-F, Zhou C.-Y, Che C.-M. Synlett 2011; 2713
• 12d Chen G.-Q, Xu Z.-J, Zhou C.-Y, Che C.-M. Chem. Commun. 2011; 47: 10963
• 12e Xu Z.-J, Fang R, Zhao C, Huang J.-S, Li G.-Y, Zhu N, Che C.-M. J. Am. Chem. Soc. 2009; 131: 4405
• 12f Deng Q.-H, Xu H.-W, Yuen AW.-H, Xu Z.-J, Che C.-M. Org. Lett. 2008; 10: 1529
• 13a Song X.-N, Yao Z.-J. Tetrahedron 2010; 66: 2589
• 13b Denmark SE, Fu J, Lawler MJ. Org. Synth. 2006; 83: 121
• 13c Alexakis A, Tomassini A, Chouillet C, Roland S, Mangeney P, Bernardinelli G. Angew. Chem. Int. Ed. 2000; 39: 4093
• 14 Kim HY, Li J.-Y, Kim S, Oh K. J. Am. Chem. Soc. 2011; 133: 20750
• 15 Robles-Machín R, González-Esguevillas M, Adrio J, Carretero JC. J. Org. Chem. 2010; 75: 233
• 16 Llamas T, Arrayás RG, Carretero JC. Org. Lett. 2006; 8: 1795
• 17 Bai J.-F, Wang L.-L, Peng L, Guo Y.-L, Ming J.-N, Wang F.-Y, Xu X.-Y, Wang L.-X. Eur. J. Org. Chem. 2011; 4472
• 18 Trunkfield AE, Gurcha SS, Besra GS, Bugg TD. H. Bioorg. Med. Chem. 2010; 18: 2651
• 19 Nakano M, Terada M. Synlett 2009; 1670