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

✍ Scribed by Dieter Enders; Dominik P. Göddertz; Christian Beceño; Gerhard Raabe

Publisher
John Wiley and Sons
Year
2010
Tongue
English
Weight
230 KB
Volume
352
Category
Article
ISSN
1615-4150

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✦ Synopsis

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 and removal of the racemates.

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