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Synfacts 2010(7): 0813-0813  
DOI: 10.1055/s-0029-1220045
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Copper-Catalyzed Addition of Grignard Reagents to N-Sulfonyl Azoalkenes

Contributor(s): Paul Knochel, Tobias Thaler
J. M. Hatcher, D. M. Coltart*
Duke University, Durham, USA
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Publication History

Publication Date:
22 June 2010 (online)

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Copper-Catalyzed Addition of Grignard Reagents to N-Sulfonyl AzoalkenesSynfacts 2010; 2010(09): 1091-1091
DOI: 10.1055/s-0030-1258045

Significance

The copper(I)-catalyzed addition of organomagnesium reagents to in situ derived N-sulfonyl azoalkenes was shown to result in an umpolung alkylation enabling the synthesis of ­extremely sterically hindered compounds that cannot be accessed via the traditional enolate chemistry.