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Short Paper | Regular issue | Vol 98, No. 5, 2019, pp.711-722
Published online, 26th April, 2019
DOI: 10.3987/COM-19-14078
Ultrafast and Diastereoselective Synthesis of 3-Spirocyclopropyl-2-oxindoles Bearing Three Continuous All-Carbon Quaternary Centers

Aixin Geng, Hao Cui, Liyuan Zhang, Tao Lu,* and Yong Zhu*

*Department of Organic Chemistry, School of Science, China Pharmaceutical University, 639 Longmian Avenue, Nanjing 211198, China

Abstract

Synthesis of 3-spirocyclopropyl-2-oxindoles bearing three continuous all-carbon quaternary centers by the domino Michael-alkylation reaction between 3-chlorooxindole and isatylidenemalononitrile is described. Remarkably, the reaction proceeded in exceptionally high efficiency (up to 99% yield within 2 min) and excellent diastereoselectivity (>25:1 dr for all the examples).