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Synfacts 2011(5): 0529-0529  
DOI: 10.1055/s-0030-1259866
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Diastereoselective Palladium-Catalyzed C(sp³)-C(sp) Cross-Couplings

Contributor(s): Hisashi Yamamoto, Kimberly Griffin
T. Thaler, L.-N. Guo, P. Mayer, P. Knochel*
Ludwig-Maximilians-Universität München, Germany and Xi’an Jiaotong University, P. R. of China
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Publication History

Publication Date:
15 April 2011 (online)

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Significance

Few synthetic methods are available for C(sp³) and C(sp) cross-coupling, due to competing β-hydride elimination and slow reductive elimination. In this report, the authors describe the palladium-catalyzed cross-coupling of cyclohexylzinc reagents with bromoalkynes. Stereoselective versions of these reactions are scarce, but the authors impressively achieve high diastereoselectivity in such cross-couplings. Dia­stereoselectivity of the cyclohexyl ring is noteworthy, and this method will be useful in the future.