Diastereoselective trans Cyclopropanation of 3-Alkylidene Oxindoles with In Situ Generated α-Diazo Carbonyls or α,β-Unsaturated Diazo Compounds

Abstract

An efficient diastereoselective trans cyclopropanation of 3-alkylidene oxindoles with in situ generated α-diazo carbonyl compounds or α,β-unsaturated diazo compounds under metal-free conditions has been developed to synthesize 3-spirocyclopropyl-2-oxindole derivatives. The procedure is based on the 1,3-dipolar character of the corresponding diazo compounds under base-catalyzed conditions. The method has a wide substrate scope and uses easily available starting materials.

Key words

diastereoselectivity - trans cyclopropanation - diazo compounds - 1,3-dipoles - spiro compounds - oxindoles

Publication History

Received: 11 December 2020

Accepted after revision: 05 February 2021

Accepted Manuscript online:
05 February 2021

Article published online:
08 March 2021

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