DOUBLE MICHAEL ADDITION OF OXINDOLES TO DIENONES CATALYZED BY TBAB: AN EFFICIENT ROUTE TO SPIROCYCLIC OXINDOLES

The efficient synthesis of biologically active spiro compounds is a challenge for organic chemists and pharmaceutical chemists. Herein we describe a synthesis strategy of spirocyclic oxindoles via double Michael reaction of N-protected-oxindoles to dienones using tetrabutylammonium bromide (TBAB) as...

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Bibliographic Details
Published inHeterocycles Vol. 102; no. 1; pp. 93 - 104
Main Authors Cao, Haiyong, Lin, Yan, Wan, Pingnan, Liu, Wenqin, Zeng, Jinxiang, Cui, Hanfeng
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 01.01.2021
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ENANTIOSELECTIVE SYNTHESIS
PHASE-TRANSFER CATALYST
ASYMMETRIC-SYNTHESIS
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Summary:The efficient synthesis of biologically active spiro compounds is a challenge for organic chemists and pharmaceutical chemists. Herein we describe a synthesis strategy of spirocyclic oxindoles via double Michael reaction of N-protected-oxindoles to dienones using tetrabutylammonium bromide (TBAB) as catalyst. The desired spirocyclic oxindoles were obtained with both high yields up to 99% and diastereoselectivity up to >95:5 dr.
ISSN:0385-5414
1881-0942
DOI:10.3987/COM-20-14364