Synthesis of Substituted Cyclopentenol Derivatives via Intramolecular Addition Reaction of Vinylcopper Species

Abstract

A new method for the synthesis of substituted cyclopentenes is developed, based on an intramolecular 1,2-addition reaction of vinylcopper species generated from 1,1-dibromoalkene derivatives. The substrates are prepared from ketones through the aldol reaction with 3,3-dibromoacrolein followed by silylation of the hydroxyl group. Treatment of the substrate with excess Me2CuLi results in the formation of 3-methyl-2-cyclopenten-1-ol derivatives with good yields.