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. 2005 Sep 2;70(18):7418-21.
doi: 10.1021/jo050257l.

Dipeptide-catalyzed asymmetric aldol condensation of acetone with (N-alkylated) isatins

Gianluigi Luppi  1 , Pier Giorgio Cozzi, Magda Monari, Bernard Kaptein, Quirinus B Broxterman, Claudia Tomasini
Affiliations

Dipeptide-catalyzed asymmetric aldol condensation of acetone with (N-alkylated) isatins

Gianluigi Luppi et al. J Org Chem. .

Abstract

[reaction: see text] 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-beta3-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.

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