C(alpha)-tetrasubstituted amino acid based peptides in asymmetric catalysis.
C(alpha)-tetrasubstituted alpha-amino acids constitute a powerful tool for controlling the conformation of short peptide sequences. Chiral peptides may be used in stereoselective reactions both for asymmetric induction and in kinetic resolution. By reviewing recent data from our own laboratories and by presenting new results on the stereoselective oxidation of chalcone to the corresponding oxide, this contribution shows that the control of peptide conformation is a critical issue in order to achieve successful stereoselective catalysis.
Licini
Giulia
G
Department of Chemical Sciences, University of Padova, 35131 Padova, Italy.
Bonchio
Marcella
M
Broxterman
Quirinus B
QB
Kaptein
Bernard
B
Moretto
Alessandro
A
Toniolo
Claudio
C
Scrimin
Paolo
P
D000215:Acylation; D000596:Amino Acids / Q000737:chemistry*; D002384:Catalysis; D002599:Chalcone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*; D047188:Chalcones; D004852:Epoxy Compounds / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D007700:Kinetics; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010455:Peptides / Q000737:chemistry*; D010626:Phenylethyl Alcohol / Q000737:chemistry; D013237:Stereoisomerism
D000596:Amino Acids; D047188:Chalcones; D004852:Epoxy Compounds; D007659:Ketones; D010455:Peptides; C028770:chalcone epoxide; D002599:Chalcone; D010626:Phenylethyl Alcohol