Allyldiisopropylphenylsilane as a synthetic equivalent of 2-hydroxy-1,3-dipole. Stereoselective synthesis of cyclopentanols

Abstract

ZrCl4-Promoted [3 + 2] cycloaddition of allyldiisopropylphenylsilane to α,β-unsaturated ketones proceeds smoothly to afford silyl-substituted cyclopentanes highly stereoselectively. Oxidative cleavage of the carbon–silicon bond leads to stereoselective formation of cyclopentanols.