Journal
ORGANIC LETTERS
Volume 13, Issue 19, Pages 5064-5067Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol201927c
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Funding
- National Natural Science Foundation of China [20802074]
- National Basic Research Program of China (973 Program) [2010CB833300]
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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.
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