Issue 26, 2010
From the journal:

Chemical Communications

Photochemical type II reaction of atropchiral benzoylformamides to point chiral oxazolidin-4-ones. Axial chiral memory leading to enantiomeric resolution of photoproducts†

Josepha L. Jesuraja  and  J. Sivaguru*a  

* Corresponding authors

a Department of Chemistry and Molecular Biology, North Dakota State University, Fargo, USA
E-mail: sivaguru.jayaraman@ndsu.edu

Abstract

Atropisomeric benzoylformamides 1 undergo Type II reaction leading to cis-2 and trans-2 oxazolidin-4-one photoproducts. The N–C(Aryl) chiral axis is maintained during the course of the phototransformation in spite the reaction proceeding through a near planar intermediate(s). As the rotational barrier of the N–C(Aryl) chiral axis in the cis-2 and trans-2 photoproducts is lowered when compared with the reactant 1, the isolated optically pure trans-2 isomer is converted to the ent-cis-2 isomer without affecting the C-5 stereogenic center, resulting in resolution of the cis-2 enantiomers.

Graphical abstract: Photochemical type II reaction of atropchiral benzoylformamides to point chiral oxazolidin-4-ones. Axial chiral memory leading to enantiomeric resolution of photoproducts

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Article information

DOI
https://doi.org/10.1039/C0CC00470G
Article type
Communication
Submitted
18 Mar 2010
Accepted
20 Apr 2010
First published
25 May 2010

Chem. Commun., 2010,46, 4791-4793

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Photochemical type II reaction of atropchiral benzoylformamides to point chiral oxazolidin-4-ones. Axial chiral memory leading to enantiomeric resolution of photoproducts

J. L. Jesuraj and J. Sivaguru, Chem. Commun., 2010, 46, 4791 DOI: 10.1039/C0CC00470G

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