Issue 77, 2013
From the journal:

Chemical Communications

Intramolecular Paternò–Büchi reaction of atropisomeric α-oxoamides in solution and in the solid-state†

Ramya Raghunathan,a   Elango Kumarasamy,a   Akila Iyer,a   Angel Ugrinova  and  J. Sivaguru*a  

* Corresponding authors

a Department of Chemistry and Biochemistry, North Dakota State University, Fargo, North Dakota 58108, USA
E-mail: sivaguru.jayaraman@ndsu.edu
Fax: +1 701-231-8831
Tel: +1 701-231-8923

Abstract

Atropisomeric α-oxoamides were synthesized and employed for intramolecular Paternò–Büchi reaction leading to very high enantio- and diastereoselectivity in the bicyclic oxetane photoproduct. A reversal of product selectivity was observed in solution and in the solid-state.

Graphical abstract: Intramolecular Paternò–Büchi reaction of atropisomeric α-oxoamides in solution and in the solid-state

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Article information

DOI
https://doi.org/10.1039/C3CC44281K
Article type
Communication
Submitted
06 Jun 2013
Accepted
26 Jul 2013
First published
20 Aug 2013

Chem. Commun., 2013,49, 8713-8715

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Intramolecular Paternò–Büchi reaction of atropisomeric α-oxoamides in solution and in the solid-state

R. Raghunathan, E. Kumarasamy, A. Iyer, A. Ugrinov and J. Sivaguru, Chem. Commun., 2013, 49, 8713 DOI: 10.1039/C3CC44281K

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