Radical Reduction Of Epoxides Using A Titanocene(Iii)/Water System: Synthesis Of Beta-Deuterated Alcohols And Their Use As Internal Standards In Food Analysis

We describe a comprehensive study into the Cp2TiCl-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 D2O as a deuterium source leads to an efficient synthesis of beta-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