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Synfacts 2010(8): 0929-0929  
DOI: 10.1055/s-0030-1257749
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

N-C Aryl Transfer via Umpolung Carbolithiation of Vinyl Ureas

Contributor(s):Paul Knochel, Tobias Thaler
J. Clayden*, M. Donnard, J. Lefranc, A. Minassi, D. J. Tetlow
University of Manchester, UK
Tandem β-Alkylation-α-Arylation of Amines by Carbolithiation and Rearrangement of N-Carbamoyl Enamines (Vinyl Ureas)
J. Am. Chem. Soc.  2010,  132:  6624-6625  
CrossrefPubMed
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Publication History

Publication Date:
22 July 2010 (online)

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Key words

carbolithiation - rearrangement - aryl migration - N-C aryl transfer - vinyl ureas - tandem reaction

Significance

The umpolung carbolithiation of ­vinyl ureas was shown to result in an N-C aryl transfer allowing a fast access to tertiary alkyl amines. Notably, (E)- and (Z)-alkenyl ureas undergo this carbolithiation-rearrangement sequence diastereospecifically.

Comment

This novel tandem reaction represents an important achievement for the synthesis of heavily substituted tertiary amines. The reaction is general, allows the use of various organolithium reagents, and proceeds with electron-rich and electron-poor aryl moieties.

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