Alkylmetal Asymmetric Reduction. 13. A Sterically Crowded Chiral Organoaluminum Compound as a Reducing Agent of Ketones

Article abstract of DOI:10.1021/jo00176a018

Optically active carbinols were obtained by reducing the corresponding ketones with <<(1S,2R)-6,6-dimethylbicyclo<3.1.1>heptan-2-yl>methyl>aluminum dichloride.The reactions, which have been carried out at room temperature, are fast and afforded the carbinols in good chemical and optical yields.The extent of the enantioselectivity, along with the stereochemistry of the process, was found to depend on the structure of the ketone employed.The overall results indicated that the present reducing method may be a convenient route to obtain secondary alcohols of high enantiomeric purity under mild conditions.