Proline-beta(3)-amino-ester dipeptides as efficient catalysts for enantioselective direct aldol reaction in aqueous medium.
Dipeptides obtained from l-proline and beta(3)-l-amino acids are reported to catalyze enantioselective direct aldol reaction in aqueous medium, leading to significant anti:syn diastereomeric ratios and enantiomeric excesses. The simple introduction of a polar substituent at the C-2 position of the beta(3)-l-amino acid was also found to enhance appreciably both diastereo- and enantioselectivity of the catalyst.
De Nisco
Mauro
M
Dipartimento di Chimica Organica e Biochimica, Università di Napoli Federico II, Via Cintia, 4 Napoli 80126, Italy. denisco@unina.it
Pedatella
Silvana
S
Ullah
Hidayat
H
Zaidi
Javid H
JH
Naviglio
Daniele
D
Ozdamar
Ozgür
O
Caputo
Romualdo
R
D000447:Aldehydes / Q000737:chemistry*; D001547:Benzaldehydes / Q000737:chemistry; D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D003512:Cyclohexanones / Q000737:chemistry; D004151:Dipeptides / Q000737:chemistry*; D004952:Esters / Q000737:chemistry*; D057927:Hydrophobic and Hydrophilic Interactions; D009682:Magnetic Resonance Spectroscopy; D011392:Proline / Q000031:analogs & derivatives / Q000737:chemistry*; D013237:Stereoisomerism; D014364:Tryptophan / Q000031:analogs & derivatives / Q000737:chemistry; D014443:Tyrosine / Q000031:analogs & derivatives / Q000737:chemistry; D014867:Water / Q000737:chemistry*
D000447:Aldehydes; D001547:Benzaldehydes; D003512:Cyclohexanones; D004151:Dipeptides; D004952:Esters; D014867:Water; D014443:Tyrosine; C029915:4-nitrobenzaldehyde; C036468:cyclohexanone; C116609:3-hydroxybutanal; D014364:Tryptophan; D011392:Proline