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Some simple and efficient routes to highly enantiomerically enriched anti-1,2-amino alcohols and syn-1,2-diols through direct asymmetric Mannich, Mannich-type, and aldol reactions involving unmodified alpha-hydroxyketones catalyzed by primary amine-containing amino acids are described. The findings present additional support for the hypothesis suggesting that amino acid catalysis played a key role in prebiotic chemistry facilitating the asymmetric synthesis of the molecules of life.