Convenient synthesis of optically active deuterated primary alcohols via deuteride reduction of acetals derived from homochiral (1R*,2R*)-3,3,3-trifluoro-1-phenylpropane-1,2-diols

(1R)-1-Deuterated alcohols with high enantiomeric excess were prepared via TiCl4/Et3SiD reduction of acetals arising from the reaction of aldehydes with (1S,2S)-3,3,3-trifluoro-1-phenylpropane-1,2-diol 9. Such a chiral auxiliary was synthesized in an enantiomerically pure form starting from L-mandelic acid. Due to its benzylic nature, it was easily removed from the reaction product of the reductive 1,3-dioxolane ring-cleavage to afford the desired alpha-deuterated alcohol. (C) 2009 Elsevier Ltd. All rights reserved.