Asymmetric synthesis of polyfunctionalized pyrrolidines via a thiourea catalyzed domino Mannich/aza-Michael reaction

Article abstract of DOI:10.1002/adsc.201000658

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 and removal of the racemates. Copyright