Intramolecular Cyclopropanation of Epichlorohydrin-Derived Unsaturated Chlorohydrins

Abstract

Concise stereoselective syntheses of bicyclo[3.1.0]hexan-2-ols and a bicyclo[4.1.0]heptan-2-ol are achieved via regioselective ring-opening of epichlorohydrin with allylic and homoallylic Grignard reagents, followed by lithium 2,2,6,6-tetramethylpiperidide-induced intramolecular cyclopropanation of the resulting unsaturated chlorohydrins.

intramolecular cyclopropanation - lithium 2,2,6,6-tetramethylpiperidide - unsaturated chlorohydrin - epichlorohydrin - Grignard reagents

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