Vicinal amino alcohols as organocatalysts in asymmetric cross-aldol reaction of ketones: Application in the synthesis of convolutamydine a

Malkov, A. V., Kabeshov, M. A., Bella, M., Kysilka, O., Malyshev, D. A., Pluhackova, K. and Kocovsky, P. (2007) Vicinal amino alcohols as organocatalysts in asymmetric cross-aldol reaction of ketones: Application in the synthesis of convolutamydine a. Organic Letters, 9(26), pp. 5473-5476. (doi: 10.1021/ol7023983)

Abstract

Leucinol and valinol have been identified as efficient organocatalysts for the aldol reaction of isatin and its derivatives (as examples of activated, non-enolizable ketones) with acetone. Uncommon mechanistic features were observed and used in the formulation of the transition state of the reaction.

• Item Type: Articles
• Keywords: 1ST TOTAL-SYNTHESIS ACETONE ALCOHOLS BRYOZOAN AMATHIA-CONVOLUTA CONDENSATION CONSTRUCTION DERIVATIVES DIAZONAMIDE-A EFFICIENT FEATURES ISATINS KETONES MANNICH ORGANOCATALYSTS PINACOL MACROCYCLIZATION CASCADE PROLINE STATE TRANSITION TRANSITION-STATE
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Malkov, Dr Andrei and Kocovsky, Professor Pavel
• Authors: Malkov, A. V., Kabeshov, M. A., Bella, M., Kysilka, O., Malyshev, D. A., Pluhackova, K., and Kocovsky, P.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Organic Letters
• ISSN: 1523-7060