Diastereo- and Enantioselective Conjugate Addition of 3-Substituted Oxindoles to Nitroolefins Catalyzed by a Chiral Ni(OAc)2-Diamine Complex under Mild Conditions

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 rang...

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Published in:Organic letters 2011-10, Vol.13 (19), p.5064-5067
Main Authors: Han, Yan-Yan, Wu, Zhi-Jun, Chen, Wen-Bing, Du, Xi-Lin, Zhang, Xiao-Mei, Yuan, Wei-Cheng
Format: Article
Language:English
Subjects:
Alkenes - chemical synthesis
Catalysis
Indoles - chemistry
Ligands
Molecular Structure
Nickel - chemistry
Nitro Compounds - chemical synthesis
Organometallic Compounds - chemistry
Stereoisomerism
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cited_by cdi_FETCH-LOGICAL-a295t-d5543f2ae0b4b71c49ed6e7468b499dfcfe472f9ce99d03efda85fab429765dd3
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creator Han, Yan-Yan
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description 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.
doi_str_mv 10.1021/ol201927c
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subjects Alkenes - chemical synthesis
Catalysis
Indoles - chemistry
Ligands
Molecular Structure
Nickel - chemistry
Nitro Compounds - chemical synthesis
Organometallic Compounds - chemistry
Stereoisomerism
title Diastereo- and Enantioselective Conjugate Addition of 3-Substituted Oxindoles to Nitroolefins Catalyzed by a Chiral Ni(OAc)2-Diamine Complex under Mild Conditions
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