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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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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cited_by cdi_FETCH-LOGICAL-a411t-f6edf7db121db19dfbd6db7ffd343c40008fe1580b0a62a4275ec858b1f3b13a3
cites cdi_FETCH-LOGICAL-a411t-f6edf7db121db19dfbd6db7ffd343c40008fe1580b0a62a4275ec858b1f3b13a3
container_end_page 11312
container_issue 24
container_start_page 11307
container_title Journal of organic chemistry
container_volume 77
creator Jin, Cheng-Yong
Wang, Yao
Liu, Yao-Zong
Shen, Chao
Xu, Peng-Fei
description 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.
doi_str_mv 10.1021/jo301886j
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source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
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
title Organocatalytic Asymmetric Michael Addition of Oxindoles to Nitroolefins for the Synthesis of 2,2-Disubstituted Oxindoles Bearing Adjacent Quaternary and Tertiary Stereocenters
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