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Communication | Regular issue | Vol 48, No. 1, 1998, pp.15-20
Published online, 1st January, 1970
DOI: 10.3987/COM-97-8007
A Novel Nucleophilic Addition to α-Fluoro-α-trifluoromethyl-γ-lactones

Ken-ichi Ogu, Yusuke Saito, Motohiro Akazome, and Katsuyuki Ogura*

*Department of Applied Chemistry, Faculty of Engineering, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan

Abstract

α-Fluoro-β-(p-tolylsulfonylmethyl)-α-trifluoromethyl-γ-lactones (2) show high reactivity for various nucleophiles to afford cyclic hemiketals (3). Reduction of 3 with lithium aluminium hydride brought about reductive ring-opening to give 2-fluoro-3-(p-tolylsulfonylmethyl)-2-(trifluoromethyl)alkane-1,4-diols (4) in a stereoselective manner.