Synfacts 2010(6): 0673-0673  
DOI: 10.1055/s-0029-1219870
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Synthesis of Fluorohydrins

Contributor(s): Mark Lautens, David A. Candito
J. A. Kalow, A. G. Doyle*
Princeton University, USA
Further Information

Publication History

Publication Date:
20 May 2010 (online)

Significance

Due to the unique properties of ­fluorinated organic molecules they are prevalent in pharmaceutically active agents. Thus, methods for the asymmetric synthesis of useful chiral ­fluorine-containing building blocks are highly sought after. The authors report a dual-catalyst system consisting of a chiral amine and a chiral (salen)Co complex for the nucleophilic epoxide ring opening with a latent source of fluoride. The protocol delivers useful fluorohydrins in superior yields and enantioselectivities under mild reaction conditions.