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Desymmetrization of Glycerol Derivatives with Peptide-Based Acylation Catalysts

2005; American Chemical Society; Volume: 7; Issue: 14 Linguagem: Inglês

10.1021/ol051061a

1523-7060

Chad A. Lewis, Bianca R. Sculimbrene, Yingju Xu, Scott J. Miller,

Microbial Natural Products and Biosynthesis

Nucleophile-loaded peptides have been evaluated as catalysts for the desymmetrization of glycerol derivatives through an enantioselective acylation process. Enantiomeric excesses of up to 97% have been obtained for the monoacylated products. A range of other substrates have been examined that shed light on the mechanistic basis of the desymmetrizations.