Issue 14, 2006

Electrostatic repulsion as an additional selectivity factor in asymmetric proline catalysis

Abstract

The metal free, single amino acid-catalyzed asymmetric desymmetrization (ADS) of meso-compounds 1 with nitrosobenzene 2 has been investigated using DFT. In this communication, we describe the role of electrostatic and dipole–dipole interactions in amino acid-catalyzed reactions, which has not previously been invoked in discussions of these important reactions.

Graphical abstract: Electrostatic repulsion as an additional selectivity factor in asymmetric proline catalysis

Supplementary files

Article information

Article type
Communication
Submitted
17 May 2006
Accepted
13 Jun 2006
First published
21 Jun 2006

Org. Biomol. Chem., 2006,4, 2685-2689

Electrostatic repulsion as an additional selectivity factor in asymmetric proline catalysis

J. Joseph, D. B. Ramachary and E. D. Jemmis, Org. Biomol. Chem., 2006, 4, 2685 DOI: 10.1039/B606996G

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