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Short Paper | Regular issue | Vol 102, No. 1, 2021, pp.93-104
Published online, 4th December, 2020
DOI: 10.3987/COM-20-14364
Double Michael Addition of Oxindoles to Dienones Catalyzed by TBAB: An Efficient Route to Spirocyclic Oxindoles

Haiyong Cao, Yan Lin, Pingnan Wan, Wenqin Liu, Jinxiang Zeng,* and Hanfeng Cui*

*School of Pharmacy, Jiangxi University of Traditional Chinese Medicine, Nanchang 330004, China

Abstract

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.