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Skotnitzki, Jun; Morozova, Varvara; Knochel, Paul (2018): Diastereoselective Copper-Mediated Cross-Couplings between Stereodefined Secondary Alkylcoppers with Bromoalkynes. In: Organic Letters, Vol. 20, No. 8: pp. 2365-2368
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A copper(I)-mediated cross-coupling of stereo defined secondary alkyllithiums with bromoalkynes provided stereodefined alkynes with high diastereoselectivity (dr up to 98:2). This cross-coupling was extended to various secondary alkyllithiums bearing a remote oxygen functionality, and the alkyne synthesis was also performed with optically enriched alkyl iodides (up to 99% ee) providing, after cross-coupling, alkynes bearing two stereocenters (dr = 93:7;up to 99% ee).