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Synlett 1995; 1995(5): 429-430
DOI: 10.1055/s-1995-5003
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Borane O-Adduct Can Be an Intermediate in Chiral N-Sulfonyloxazaborolidine-Catalyzed Enantioselective Reduction of Ketones

Kazuhiro Otsuka, Katsuji Ito, Tsutomu Katsuki*
  • *Department of Chemistry, Faculty of Science, Kyushu University 33, Hakozaki, Higashi-ku, Fukuoka 812, Japan
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Publication Date:
31 December 2000 (online)

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Chiral N-sulfonylamino alcohols were found to serve as an effective chiral source in the borane reduction of ketones, though stoichiometric. Contrary to the previous report, this result suggests that borane and N-sulfonyloxazaborolidine form a complex (borane O-adduct) and that the borane O-adduct reduces ketones enantioselectively.

enantioselective reduction - chiral N-sulfonyloxazaborolidine - borane O-adduct