Issue 14, 2006
From the journal:

Organic & Biomolecular Chemistry

Electrostatic repulsion as an additional selectivity factor in asymmetric proline catalysis†

Jorly Joseph,ab   Dhevalapally B. Ramachary*a  and  Eluvathingal D. Jemmis*b  

* Corresponding authors

a School of Chemistry, University of Hyderabad, Hyderabad, India
E-mail: ramsc@uohyd.ernet.in
Fax: +91-40-23012460

b Department of Inorganic and Physical Chemistry, Indian Institute of Science, Bangalore, India
E-mail: jemmis@ipc.iisc.ernet.in
Fax: +91-80-23601552

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

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Article information

DOI
https://doi.org/10.1039/B606996G
Article type
Communication
Submitted
17 May 2006
Accepted
13 Jun 2006
First published
21 Jun 2006

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

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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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