In recent years, new developments in the area of stereoselective reduction of cyclic ketones have been exceptionally encouraging. Especially, the reagents developed for conversion of cyclic ketones to the thermodynamically less stable alcohols are extraordinary. 1 However, although several useful reagents have been devised for converting cyclic ketones to the thermodynamically more stable alcohols, 2 generally acceptable synthetic methods for this conversion have still been lacking. In the course of a systematic study of the reducing characteristics of Al-alkoxydiisobutylalane, we have found that Al-isopropoxydiisobutylalane, one of these derivatives, reveals an excellent stereoselectivity in such cyclic ketone reductions to provide the corresponding thermodynamically more stable alcohols. This paper describes this stereoselective reduction.

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