Organocatalytic Asymmetric Michael Addition of Oxindoles to Nitroolefins for the Synthesis of 2,2-Disubstituted Oxindoles Bearing Adjacent Quaternary and Tertiary Stereocenters

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 stereoselectivitie...

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Bibliographic Details
Published in:Journal of organic chemistry 2012-12, Vol.77 (24), p.11307-11312
Main Authors: Jin, Cheng-Yong, Wang, Yao, Liu, Yao-Zong, Shen, Chao, Xu, Peng-Fei
Format: Article
Language:English
Subjects:
Alkenes - chemistry
Catalysis
Catalysts: preparations and properties
Chemistry
Chemistry Techniques, Synthetic
Exact sciences and technology
General and physical chemistry
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Indoles - chemical synthesis
Indoles - chemistry
Nitro Compounds - chemistry
Organic chemistry
Preparations and properties
Stereoisomerism
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo301886j