Synfacts 2010(4): 0428-0428  
DOI: 10.1055/s-0029-1219481
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Diastereoselective Negishi Coupling of Cycloalkylzinc Reagents

Contributor(s): Mark Lautens, Stephen G. Newman
T. Thaler, B. Haag, A. Gavryushin, K. Schober, E. Hartmann, R. M. Gschwind, H. Zipse, P. Mayer, P. Knochel*
Ludwig-Maximilians-Universität München, Germany
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Publikationsdatum:
22. März 2010 (online)

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Significance

The use of sp³-hybridized carbon nucleophiles is becoming more common in cross-coupling reactions. The authors present an sp³-sp² Negishi cross-coupling protocol that allows for the synthesis of disubstituted cyclohexanes with high diastereoselectivity. Substituents as small as a methyl group on the ring are sufficient to induce high selectivity.