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.
Lewis
Chad A
CA
Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA.
Sculimbrene
Bianca R
BR
Xu
Yingju
Y
Miller
Scott J
SJ
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