Highly diastereoselective Csp3–Csp2 Negishi cross-coupling with 1,2-, 1,3- and 1,4-substituted cycloalkylzinc compounds

Highly diastereoselective Negishi cross-coupling reactions between 2-, 3- and 4-substituted cycloalkylzinc reagents and aryl iodides are described. In all cases, the thermodynamically most stable diastereomers of the cross-coupling products were obtained. NMR spectroscopy and density functional theory calculations were performed in order to rationalize the observed stereoselectivities.