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Pyrrolidine-based amino alcohols: novel ligands for the enantioselective alkyla...

A series of easily obtained pyrrolidine-based [beta]-amino alcohols derived from tartaric acid and primary amines was synthesized and used as chiral ligands in the enantioselective alkylation of benzaldehyde. Using diethylzinc, 1-phenyl-1-propanol was obtained with enantiomeric excesses of up to 80% when (3S,4S)-N-(1-naphthylmethyl)-3,4-dihydroxypyrrolidine was used. The nature of the N-substituent on the ligan...