Construction of highly enantioenriched spirocyclopentaneoxindoles containing four consecutive stereocenters via thiourea-catalyzed asymmetric Michael-Henry cascade reactions

The thiourea-catalyzed asymmetric synthesis of highly enantioenriched spirocyclopentaneoxindoles containing chiral amide functional groups using simple 3-substituted oxindoles and nitrovinylacetamide as starting materials was achieved successfully. This protocol features operational simplicity, high...

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Bibliographic Details
Published in:Beilstein journal of organic chemistry 2017-07, Vol.13 (1), p.1342-1349
Main Authors: Du, Yonglei, Li, Jian, Chen, Kerong, Wu, Chenglin, Zhou, Yu, Liu, Hong
Format: Article
Language:English
Subjects:
Asymmetric synthesis
Chemistry
four consecutive stereocenters
Full Research Paper
Investigations
Michael–Henry cascade reactions
Natural products
Solvents
spirocyclopentaneoxindoles
Thiourea
thioureas
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Summary:The thiourea-catalyzed asymmetric synthesis of highly enantioenriched spirocyclopentaneoxindoles containing chiral amide functional groups using simple 3-substituted oxindoles and nitrovinylacetamide as starting materials was achieved successfully. This protocol features operational simplicity, high atom economy, and high catalytic asymmetry, thus representing a versatile approach to the synthesis of highly enantioenriched spirocyclopentaneoxindoles.
ISSN:1860-5397
2195-951X
1860-5397
DOI:10.3762/bjoc.13.131