Asymmetric Synthesis of Polyfunctionalized Pyrrolidines via a Thiourea Catalyzed Domino Mannich/Aza??Michael Reaction

D Enders, DP Goeddertz, C Beceno…

Index: Enders, Dieter; Goeddertz, Dominik P.; Beceno, Christian; Raabe, Gerhard Advanced Synthesis and Catalysis, 2010 , vol. 352, # 17 p. 2863 - 2868

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Citation Number: 32

Abstract

Abstract The domino Mannich/aza-Michael reaction of γ-malonate-substituted α, β- unsaturated esters with N-protected arylaldimines has been achieved. Catalyzed by bifunctional thioureas, 2, 5-cis-configured polysubstituted pyrrolidines are obtained in good to excellent yields (76–99%), enantioselectivities (75–94%) and excellent diastereoselectivities (de> 95%). The pure stereoisomers are available by crystallization ...

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