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Asymmetric Synthesis of Polyfunctionalized Pyrrolidines via a Thiourea Catalyzed Domino Mannich/Aza‐Michael Reaction
Author(s) -
Enders Dieter,
Göddertz Dominik P.,
Beceño Christian,
Raabe Gerhard
Publication year - 2010
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201000658
Subject(s) - chemistry , thiourea , bifunctional , domino , michael reaction , mannich reaction , catalysis , organic chemistry , cascade reaction , malonate , dimethyl malonate , combinatorial chemistry , enantioselective synthesis
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.