Desymmetrization of glycerol derivatives with peptide-based acylation catalysts.
[reaction: see text] 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.
Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA.
Chad A
CA
Lewis
Bianca R
BR
Sculimbrene
Yingju
Y
Xu
Scott J
SJ
Miller
D000215:Acylation; D002384:Catalysis; D005990:Glycerol / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D007202:Indicators and Reagents; D008049:Lipase / Q000378:metabolism; D015394:Molecular Structure; D010455:Peptides / Q000737:chemistry*; D011549:Pseudomonas / Q000201:enzymology; D013237:Stereoisomerism
D007202:Indicators and Reagents; D010455:Peptides; D008049:Lipase; D005990:Glycerol