Issue 15, 2013
From the journal:

Chemical Communications

Reversible aryl migrations in metallated ureas: controlled inversion of configuration at a quaternary carbon atom†

Daniel J. Tetlow,a   Mark A. Vincent,a   Ian H. Hilliera  and  Jonathan Clayden*a  

* Corresponding authors

a School of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, UK
E-mail: clayden@man.ac.uk
Fax: +44 (0)161 275 4939

Abstract

Deprotonation with strong bases of N-vinyl ureas carrying an N′-aryl substituent leads to migration of the N′-aryl group from N to C via an allyllithium; with weaker bases and electron-deficient aryl rings the direction of the migration reverses, and aryl substituents α to the urea N atom may migrate from C to N.

Graphical abstract: Reversible aryl migrations in metallated ureas: controlled inversion of configuration at a quaternary carbon atom

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Article information

DOI
https://doi.org/10.1039/C2CC38704B
Article type
Communication
Submitted
04 Dec 2012
Accepted
02 Jan 2013
First published
03 Jan 2013

Chem. Commun., 2013,49, 1548-1550

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Reversible aryl migrations in metallated ureas: controlled inversion of configuration at a quaternary carbon atom

D. J. Tetlow, M. A. Vincent, I. H. Hillier and J. Clayden, Chem. Commun., 2013, 49, 1548 DOI: 10.1039/C2CC38704B

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