Synthetic Applications of the Enantioselective Reduction by Binaphthol-Modified Lithium Aluminum Hydride Reagents

Article abstract of DOI:10.1021/ja00334a042

The reduction of prochiral carbonyl substrates with the chiral binaphthol-modified lithium aluminum hydride reagents provides an effective means for preparing alcoholic products of high optical purity.The reaction is applicable to a variety of structurally diverse unsaturated carbonyl compounds such as aromatic ketones, acetylenic ketones, olefinic ketones and aldehydes, etc.Either of the antipodes is obtainable in a predictable manner by choosing the handedness of the auxiliary binaphthol ligand.The utility is exemplified by the efficiently stereocontrolled synthesis of prostaglandin intermediates, some insect pheromones, chiral primary terpenic alcohols, optically active styrene oxide, etc.