Asymmetric reduction of carbonyl compounds with chiral alkoxyaluminium and alkoxymagnesium halides: an overview

Abstract

A summary of the work on asymmetric reduction of carbonyl compounds with chiral alkoxyaluminium and alkoxymagnesium halides derived mainly fromexo- andendo-bornan-2-ols done in the present laboratory has been given. The highlights of the contributions are as follows: (i) the development of a new class of extremely enantioselective and diastereoselective reducing reagents which are easily accessible, (ii) practical synthesis ofa-deuterated benzyl alcohol, 2,2,2-trifluoro-1-phenylcthanol (a chiralnmr solvent) and some aminoalcohols of physiological importance in high chemical and optical yields, (iii) a new chemical method to determine the configuration of chiral ketones and (iv) a highly satisfactory transition state model for these reactions which explains all the literature data so far.