Dipeptide-Catalyzed Asymmetric Aldol Condensation of Acetone with (N-Alkylated) Isatins

The aldol condensation of acetone with several isatins is described. The desired compound was obtained in quantitative yield and with good enantioselectivities up to 77%. The best results were obtained with 10 mol % H-d-Pro-l-β3-hPhg-OBn as a catalyst, resulting in the preferential formation of the...

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Veröffentlicht in:	Journal of organic chemistry 2005-09, Vol.70 (18), p.7418-7421
Hauptverfasser:	Luppi, Gianluigi, Cozzi, Pier Giorgio, Monari, Magda, Kaptein, Bernard, Broxterman, Quirinus B, Tomasini, Claudia
Format:	Artikel
Sprache:	eng
Schlagworte:	Catalysis Catalysts: preparations and properties Chemistry Exact sciences and technology General and physical chemistry Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Organic chemistry Peptides Preparations and properties Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
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Beschreibung
Zusammenfassung:	The aldol condensation of acetone with several isatins is described. The desired compound was obtained in quantitative yield and with good enantioselectivities up to 77%. The best results were obtained with 10 mol % H-d-Pro-l-β3-hPhg-OBn as a catalyst, resulting in the preferential formation of the (R)-enantiomer. The absolute configuration of the newly formed chiral center has been assigned by an X-ray diffraction study and CD spectra analysis of the molecules.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo050257l