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

The Journal of organic chemistry (2005-08-27)
Gianluigi Luppi, Pier Giorgio Cozzi, Magda Monari, Bernard Kaptein, Quirinus B Broxterman, Claudia Tomasini
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Acetone, ACS reagent, ≥99.5%
Sigma-Aldrich
Acetone, HPLC Plus, for HPLC, GC, and residue analysis, ≥99.9%
Sigma-Aldrich
Acetone, suitable for HPLC, ≥99.9%
Sigma-Aldrich
Acetone, suitable for HPLC, ≥99.8%
Sigma-Aldrich
Acetone, puriss. p.a., ACS reagent, reag. ISO, reag. Ph. Eur., ≥99.5% (GC)
Sigma-Aldrich
Acetone, Laboratory Reagent, ≥99.5%
Sigma-Aldrich
Acetone, suitable for HPLC, ≥99.9%
Sigma-Aldrich
Acetone, puriss., meets analytical specification of Ph. Eur., BP, NF, ≥99% (GC)