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Synfacts 2010(8): 0929-0929
DOI: 10.1055/s-0030-1257749
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 ThalerJ. 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
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
Further Information
Publication History
Publication Date:
22 July 2010 (online)
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.