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Simple Chiral Pyrrolidine–Pyridine‐Based Catalysts for Highly Enantioselective Michael Addition to Nitro Olefins
Author(s) -
Xu DaZhen,
Shi Sen,
Wang Yongmei
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900716
Subject(s) - chemistry , pyrrolidine , enantioselective synthesis , nitro , michael reaction , pyridine , aldehyde , catalysis , organic chemistry , organocatalysis , substrate (aquarium) , alkyl , oceanography , geology
A new class of chiral pyrrolidine–pyridine‐based organocatalysts, available from commercially available starting materials, have been synthesized and shown to be very effective catalysts for the asymmetric Michael addition reactions of cyclic/acyclic/aromatic ketones and an aldehyde with nitro olefins, giving excellent yields (up to 99 %), diastereoselectivities ( syn / anti = 99:1), and enantioselectivities (up to 99 %). Based on the experimental results and ESI‐MS analysis of the intermediates, the mode of activity of the organocatalyst with the substrate was deduced. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)