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Synfacts 2011(11): 1235-1235  
DOI: 10.1055/s-0030-1261074
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Lithium Cuprate Ion Pairs as a Key to Control Diastereoselectivity

Contributor(s): Paul Knochel, Andreas K. Steib
E. Vrancken*, H. Gérard*, D. Linder, S. Ouizem, N. Alouane, E. Roubineau, K. Bentayeb, J. Marrot, P. Mangeney
Institut Charles Gerhardt Montpellier, Université Pierre e Marie Curie - Paris 06 and Université de Versailles, France
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Publication History

Publication Date:
19 October 2011 (online)

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Significance

The authors describe a new diastereoselective reaction of allenyl(cyano)- and allenyl(alkyl)cuprates with aldehydes to furnish both syn- and anti-homopropargylic alcohols. The lithium cations present in the reaction mixture act as Lewis acid activators but also control the diaste­reoselectivity of the reaction.