Proline−β3-Amino-Ester Dipeptides as Efficient Catalysts for Enantioselective Direct Aldol Reaction in Aqueous Medium

Dipeptides obtained from l-proline and β3-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 β3-l-a...

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Veröffentlicht in:Journal of organic chemistry 2009-12, Vol.74 (24), p.9562-9565
Hauptverfasser: De Nisco, Mauro, Pedatella, Silvana, Ullah, Hidayat, Zaidi, Javid H, Naviglio, Daniele, Özdamar, Özgür, Caputo, Romualdo
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Sprache:eng
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Zusammenfassung:Dipeptides obtained from l-proline and β3-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 β3-l-amino acid was also found to enhance appreciably both diastereo- and enantioselectivity of the catalyst.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo902106r