Asymmetric Ring Opening of Symmetrical Epoxides with Trimethylsilyl Azide Using Chiral Titanium Complexes

Abstract

Asymmetric ring opening of cyclohexene oxide with trimethylsilyl azide was promoted by the use of catalytic amounts of chiral titanium complexes [Ti(OiPr)₄ dialkyl (+)-L-tartrates or TiCl₂(OiPr)₂-dialkyl (+)-L-tartrates] to afford trans-2-azido-cyclohexanol in up to 63% optical yield.