1,1-Dichloro-2,2,2-trifluoroethyllithium in Asymmetric Synthesis, II. A Route to Optically Pure 4,4,4-Trifluoro-2-hydroxybutanoic Acid

A. Solladié-Cavallo; S. Quazzotti

doi:10.1055/s-1991-26412

Synthesis 1991; 1991(2): 177-180
DOI: 10.1055/s-1991-26412

paper

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1,1-Dichloro-2,2,2-trifluoroethyllithium in Asymmetric Synthesis, II. A Route to Optically Pure 4,4,4-Trifluoro-2-hydroxybutanoic Acid

A. Solladié-Cavallo^* , S. Quazzotti

^*Laboratoire de Stéréochimie Organométallique associé au CNRS, E.H.I.C.S., 1 rue B. Pascal, F-67008 Strasbourg, France

Abstract

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On addition of pre-cooled butyllithium to 1,1,1-trichloro-2,2,2-trifluoroethane (1) in diethyl ether at - 125°C, 1,1-dichloro-2,2,2-trifluoroethyllithium (2) is formed, addition of o-substituted benzaldehydes yields 1-aryl-2,2-dichloro-3,3,3-trifluoropropanols, whilst addition of the chiral chromium complexes of substituted benzaldehydes yields optically pure alcohols in high yield. After decomplexation, dechlorination, protection and oxidation, optically pure (S)-2-tert-butyldimethylsiloxy-4,4,4-trifluorobutanoic acid was obtained.

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