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Synlett 1996; 1996(1): 57-59
DOI: 10.1055/s-1996-5325
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Preparation of Trifluoromethyl Lactol Derivatives via Base-Initiated Cyclobutanol Ring-Opening to a Laterally-Lithiated Trifluoromethyl Ketone

Daniel P. Becker* , Daniel L. Flynn
  • *Department of Chemistry, Searle Research & Development, 4901 Searle Parkway, Skokie, IL 60077, USA
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Publication Date:
31 December 2000 (online)

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Benzocyclobutenone derivatives 4 are converted to the corresponding trifluoromethylcyclobutanols 5 by treatment with trifluoromethyltrimethylsilane in the presence of tetra-n-butylammonium fluoride. These trifluoromethylcyclobutanol derivatives are then treated with LiTMP in the presence of aromatic aldehydes to afford trifluoromethyllactols 6 via a laterally-lithiated trifluoromethylketone intermediate.

lateral lithiation - trifluoromethyl ketone - trifluoromethyl lactol - base-induced cyclobutanol ring opening