Dipeptide-Catalyzed Asymmetric Aldol Condensation of Acetone with (N-Alkylated) Isatins
- 5 August 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 70 (18) , 7418-7421
- https://doi.org/10.1021/jo050257l
Abstract
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.Keywords
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