Chiral oxazaborolidines bearing a 1- or 2-naphthylmethyl group as catalysts for the enantioselective borane reduction of ketones: experimental and quantum chemical calculations |
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| Institution: | 1. RTI International, Center for Drug Discovery, Research Triangle Park, NC, USA;4. University of Wisconsin-Milwaukee, Chemistry Department, Milwaukee, WI, USA |
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| Abstract: | Two new catalysts for the enantioselective reduction of ketones, chiral 1,3,2-oxazaborolidines substituted at carbon 4 by a 1- or 2-naphthylmethyl group, have been prepared from the related amino alcohols, by treatment with borane in tetrahydrofuran, and the effectiveness of these two catalysts has been investigated. The stereochemical outcomes were verified by means of quantum calculations using the AM1 computational method. |
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