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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Published in | Heterocycles Vol. 102; no. 1; pp. 93 - 104 |
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Main Authors | , , , , , |
Format | Journal Article |
Language | English |
Published |
OXFORD
Elsevier
01.01.2021
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Subjects | |
Online Access | Get more information |
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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. |
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ISSN: | 0385-5414 1881-0942 |
DOI: | 10.3987/COM-20-14364 |