Synlett 2007(3): 0439-0442  
DOI: 10.1055/s-2007-968031
LETTER
© Georg Thieme Verlag Stuttgart · New York

Direct Trifluoroacetylation Across a Trimethylsilyloxy System as a Stereo­specific, Chemo- and Regioselective Approach to C3-Vicinal Halohydrins

Stephan D. Stamatov*a, Jacek Stawinski*b,c
a Department of Chemical Technology, University of Plovdiv, 24 Tsar Assen St., Plovdiv 4000, Bulgaria
b Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 10691 Stockholm, Sweden
e-Mail: js@organ.su.se;
c Institute of Bioorganic Chemistry, Polish Academy of Sciences, Noskowskiego 12/14, 61704 Poznan, Poland
Further Information

Publication History

Received 11 November 2006
Publication Date:
07 February 2007 (online)

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Abstract

Trifluoroacetylation across the silyloxy system of 1-acyl-2-O-trimethylsilyl-3-haloglycerols with trifluoroacetic anhydride (TFAA) in the presence of a halide anion (e.g. Bu4NX; X = Cl, Br or I), followed by removal of the trifluoroacetyl transient protection, provides a new, efficient entry to configurationally pure C3-vicinal halohydrins.