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Stereocontrolled creation of adjacent quaternary and tertiary stereocenters by a catalytic conjugate addition
Journal article   Peer reviewed

Stereocontrolled creation of adjacent quaternary and tertiary stereocenters by a catalytic conjugate addition

Hongming Li, Yi Wang, Liang Tang, Fanghui Wu, Xiaofeng Liu, Chengyun Guo, Bruce M Foxman and Li Deng
Angewandte Chemie (International ed.), Vol.44(1), pp.105-108
12/17/2004
PMID: 15565669

Abstract

Alkenes - chemistry Hydrogen Bonding Stereoisomerism Nitro Compounds - chemistry Crystallography, X-Ray Indicators and Reagents Nitro Compounds - chemical synthesis Molecular Structure Catalysis Alkenes - chemical synthesis
Not too close for comfort: Practical chiral organocatalysts like that shown promote Michael addition reactions of a wide range of trisubstituted carbon nucleophiles to various nitroalkenes, often with nearly perfect stereoselectivity (>99 % ee and >98:2 d.r.). In one step adjacent carbon‐ or heteroatom‐substituted quaternary and tertiary stereocenters are generated from readily available starting materials.

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