The direct amino acid-catalyzed asymmetric incorporation of molecular oxygen to organic compounds

Abstract

We have disclosed the direct catalytic incorporation of 1O2 to aldehydes. The unprecedented amino acid-catalyzed asymmetric α-oxidation of aldehydes with molecular oxygen or air proceeded with high chemoselectivity and was a direct entry for the synthesis of both enantiomers of terminal diols. The results demonstrated that simple amino acids accomplished catalytic asymmetric oxidations with molecular oxygen or air, which has previously been considered to be in the domain of enzymes and chiral transition-metal complexes. The efficiency of the catalytic process may warrant the existence of an ancient pathway for the synthesis of hydroxylated organic compounds. Copyright © 2004 American Chemical Society.