Issue 19, 2013
From the journal:

RSC Advances

Tandem oxidative radical fragmentation–rearrangement of 2-amino-1,3-benzylidene acetals: a short entry to densely functionalised fully differentiated oxazolidinones†

James McNulty*a  and  Janice Calzavaraa  

* Corresponding authors

a Department of Chemistry and Chemical Biology, McMaster University, 1280 Main Street West, L8S 4M1, Hamilton, ON, Canada
E-mail: jmcnult@mcmaster.ca
Fax: 905-522-2509
Tel: 905-525-9140 Ext. 27393

Abstract

The discovery of a novel tandem fragmentation–rearrangement process from N-Boc-protected benzylidene acetals is reported. The reaction proceeds via free-radical initiation and terminates through a 5-exo-tet ionic fragmentation process leading to biologically useful, densely functionalised oxazolidinones.

Graphical abstract: Tandem oxidative radical fragmentation–rearrangement of 2-amino-1,3-benzylidene acetals: a short entry to densely functionalised fully differentiated oxazolidinones

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Article information

DOI
https://doi.org/10.1039/C3RA40218E
Article type
Communication
Submitted
14 Jan 2013
Accepted
05 Mar 2013
First published
07 Mar 2013

RSC Adv., 2013,3, 6771-6774

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Tandem oxidative radical fragmentation–rearrangement of 2-amino-1,3-benzylidene acetals: a short entry to densely functionalised fully differentiated oxazolidinones

J. McNulty and J. Calzavara, RSC Adv., 2013, 3, 6771 DOI: 10.1039/C3RA40218E

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