The Journal of Organic Chemistry

A new class of enantioselective organoboron reducing agents. Borane complexes with chiral terpenic 1, 2-azaboracyclohexanes

MM Midland, A Kazubski

Index: Midland, M. Mark; Kazubski, Aleksander Journal of Organic Chemistry, 1992 , vol. 57, # 10 p. 2953 - 2956

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Citation Number: 21

Abstract

'19 I 2 0 reduce ketones at room temperature in THF without the presence of a Lewis acid. The increased reactivity of the borane complexes may be explained in the same manner as proposed by Corey for reductions with chiral oxazaborolidine-BH, complexes. 2 Thus, the boron of the cyclic azaborane compound presumably complexes the carbonyl oxygen and activates it toward reduction. Freshly distilled liquid azaboracyclohexanes 9-13 exist ...