Diastereo- and Enantioselective Conjugate Addition of 3-Substituted Oxindoles to Nitroolefins Catalyzed by a Chiral Ni(OAc)<sub>2</sub>-Diamine Complex under Mild Conditions
Organic LettersPublished 31 August 2011
Yanyan Han, Zhijun Wu, Wenbing Chen, Xilin Du, Xiaomei Zhang, Wei‐Cheng Yuan
Citations77
SJR quartileQ1
SJR score1.24
SNIP1.03
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TL;DR
A simple catalyst system assembled from an enantiomerically pure diamine ligand and Ni(OAc)(2) efficiently generates chiral metal enolates derived from 3-substituted oxindoles bearing an N-1 carbonyl group under mild reaction conditions.
Abstract
A simple catalyst system assembled from an enantiomerically pure diamine ligand and Ni(OAc)(2) efficiently generates chiral metal enolates derived from 3-substituted oxindoles bearing an N-1 carbonyl group. The enolates smoothly undergo diastereo- and enantioselective conjugate addition to a wide range of nitroolefins under mild reaction conditions, furnishing 3,3-disubstituted oxindole products bearing two vicinal quaternary/tertiary stereocenters in 74-95% yields and 60:40 to 99:1 dr, 71-97% ee.
Keywords
Chemistry
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