Simple Chiral Pyrrolidine–Pyridine‐Based Catalysts for Highly Enantioselective Michael Addition to Nitro Olefins | Zendy

Xu DaZhen | Zendy; Shi Sen | Zendy; Wang Yongmei | Zendy

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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)

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