Organocatalytic asymmetric Michael addition of oxindoles to nitroolefins for the synthesis of 2,2-disubstituted oxindoles bearing adjacent quaternary and tertiary stereocenters.

J Org Chem

State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China.

Published: December 2012


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Article Abstract

A bifunctional thiourea-catalyzed Michael addition of activated indolin-3-ones to nitroolefins has been developed. The synthetically useful 2,2-disubstituted indolin-3-one derivatives with vicinal chiral quaternary-tertiary stereocenters were obtained in high yields with excellent stereoselectivities. The adduct can be readily transformed into a structurally interesting heterocyclic architecture by means of further synthetic elaboration.

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