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

Daniel J. Tetlow; Mark A. Vincent; Ian H. Hillier; Jonathan Clayden

doi:10.1039/C2CC38704B

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Chemical Communications

Issue 15, 2013

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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. Hillier^a and Jonathan Clayden*^a

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

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

DOI: 10.1039/C2CC38704B
Received 04 Dec 2012, Accepted 02 Jan 2013
First published online 03 Jan 2013

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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.

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

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