Radical Reduction of Epoxides Using a Titanocene(III)/Water System: Synthesis of β‐Deuterated Alcohols and Their Use as Internal Standards in Food Analysis

Abstract We describe a comprehensive study into the Cp 2 TiCl‐mediated reductive epoxide ring opening using either water as a hydrogen source or deuterium oxide as a deuterium source. The remarkable chemical profile of this reaction allows access to alcohols with anti‐Markovnikov regiochemistry from different epoxides. The use of D 2 O as a deuterium source leads to an efficient synthesis of β‐deuterated alcohols, including a deuterated sample of tyrosol, a bioactive compound contained in the leaves of the olive, which was successfully applied as an internal standard in food analysis.