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Short Paper | Special issue | Vol 103, No. 2, 2021, pp.1048-1056
Published online, 10th February, 2021
DOI: 10.3987/COM-20-S(K)57
Chiral Phosphine Oxide-Catalyzed Enantioselective Ring Opening of Oxetanes

Shunsuke Kotani,* Yuka Tashima, Hiroki Tanaka, Shohei Aoki, and Makoto Nakajima*

*Graduate School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Chuo-ku, Kumamoto, Japan

Abstract

Chiral phosphine oxide as a Lewis base could effectively catalyze the enantioselective ring opening of 3-substituted oxetanes with silicon tetrachloride in the presence of N,N-diisopropylethylamine, affording the corresponding 2-substituted 1,3-chlorohydrins in high yields and good enantioselectivities.