A series of new C2-symmetric amino alcohols with multicoordination groups: promising catalysts for synthesis of both enantiomers in the borane-mediated reduction of prochiral ketones.

A series of new C(2)-symmetric amino alcohols with multicoordination groups have been synthesized and successfully applied as catalysts in the borane asymmetric reduction of prochiral ketones in refluxing toluene, providing the corresponding secondary alcohols with up to 90% ee. An unusual temperature-dependent reversal of stereochemistry was also observed. 2008 Wiley-Liss, Inc.