Radical reduction of epoxides using a titanocene(III)/water system: Synthesis of β-deuterated alcohols and their use as internal standards in food analysis

Article abstract of DOI:10.1002/ejoc.201000487

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 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.