Amino acids catalyze the asymmetric incorporation of molecular oxygen to organic compounds

ORGN 759

Magnus Engqvist, engqvist@organ.su.se, Henrik Sundén, Ismail Ibrahem, isse@organ.su.se, Jesus Casas, jesus.casas@organ.su.se, and Armando Córdova, acordova@organ.su.se. Department of Organic chemistry, Stockholm University, Svante Arrhenius v. 12, Sockholm, SE 106 91, Sweden
We present the direct catalytic incorporation of singlet molecular oxygen to aldehydes and ketones. The unprecedented amino acid-catalyzed asymmetric alpha oxidation of aldehydes and ketones with molecular oxygen or air proceeded with high chemoselectivity. The in situ reduction of the corresponding alpha-hydroxylated aldehydes was a direct entry for the synthesis of both enantiomers of vicinal 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 for an ancient pathway for the synthesis of hydroxylated organic compounds.

 

Asymmetric Reactions, Molecular Recognition, Self Assembly, Bioorganic Chemistry, Process R&D
8:00 PM-10:00 PM, Wednesday, 16 March 2005 Convention Center -- Hall D, Poster

Division of Organic Chemistry

The 229th ACS National Meeting, in San Diego, CA, March 13-17, 2005