It is desirable and practical to produce both enantiomers of a target from the same chiral starting material by stereodifferentiation of prochiral compounds, for instance utilizing a chiral ligand derived from a natural (L) amino acid. During the past 7 years, excellent results have been achieved in several cases by multiple stereodifferentiation of chiral ligands derived from (S)-indoline-2-carboxylic acid: highly diastereo- and enantioselective pinacol coupling reactions of chiral alpha-ketoamides gave both (S,S)- and (R,R)-quaternary tartaric acid for the first time; asymmetric Diels-Alder cyclization of chiral acrylamides in the presence of Lewis acid afforded extremely high diastereoselectivities of both opposite configurations of the cyclized diastereomers depending upon the structures of chiral ligands and Lewis acids; and asymmetric alkylation of aldehydes to both enantiomers of secondary alcohols and asymmetric hydrogenation of ketones to both enantiomers of chiral secondary alcohols have been achieved using catalysts derived from (S)-indoline-2-carboxylic acid.
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