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...

Full description

Saved in:
Bibliographic Details
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
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol201927c