Conformational change in a urea catalyst induced by sodium cation and its effect on enantioselectivity of a Friedel-Crafts reaction

Chittoory, Arjun K., Kumari, Gayatri, Mohapatra, Sudip, Kundu, Partha P., Maji, Tapas K., Narayana, Chandrabhas and Rajaram, Sridhar 2014, Conformational change in a urea catalyst induced by sodium cation and its effect on enantioselectivity of a Friedel-Crafts reaction, Tetrahedron, vol. 70, no. 21, pp. 3459-3465, doi: 10.1016/j.tet.2014.03.068.

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Title Conformational change in a urea catalyst induced by sodium cation and its effect on enantioselectivity of a Friedel-Crafts reaction
Author(s) Chittoory, Arjun K.
Kumari, Gayatri
Mohapatra, Sudip
Kundu, Partha P.
Maji, Tapas K.
Narayana, Chandrabhas
Rajaram, Sridhar
Journal name Tetrahedron
Volume number 70
Issue number 21
Start page 3459
End page 3465
Total pages 7
Publisher Elsevier
Place of publication Oxford, Eng.
Publication date 2014-05-27
ISSN 0040-4020
1464-5416
Keyword(s) sulfonyl urea
hydrogen-bonding catalysts
conformational control
IR and Raman spectroscopy
Summary While developing bis-camphorsulfonyl urea as a hydrogen-bonding catalysts, we discovered that the native conformation of the catalyst is unsuitable for inducing enantioselectivity. By complexing the catalyst with weakly Lewis acidic sodium cations, we were able to change the conformation of the catalyst and attain a significant improvement in the selectivity. We provide structural information from X-ray crystallography to show that the uncomplexed catalyst is indeed in an unfavorable conformation. Infrared and Raman spectroscopic studies show that sodium binds the catalyst through the carbonyl and sulfonyl groups. Simulated IR and Raman spectra match well with the experimentally recorded spectra, thereby corroborating the proposed conformational change. This result shows that weak Lewis acids can be used to tune the conformation of hydrogen-bonding catalysts and enhance the selectivity of reaction catalyzed by these systems.
Language eng
DOI 10.1016/j.tet.2014.03.068
Field of Research 030299 Inorganic Chemistry not elsewhere classified
030199 Analytical Chemistry not elsewhere classified
0305 Organic Chemistry
0304 Medicinal And Biomolecular Chemistry
Socio Economic Objective 970103 Expanding Knowledge in the Chemical Sciences
HERDC Research category C1.1 Refereed article in a scholarly journal
ERA Research output type C Journal article
Copyright notice ©2014, Elsevier
Persistent URL http://hdl.handle.net/10536/DRO/DU:30088560

Document type: Journal Article
Collection: School of Life and Environmental Sciences
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