the conjugate addition of BuCu·BF3 to the enoate (5) produces predominantly the syn-isomer (7) having the butyl and methyl groups syn on the carbon chain, while the methylation of the enolate derived from the ester (8) gives preferentially the other diastereoisomer, anti-(6); the diastereoselectivity can be explained by an eclipsed model.
Y. Yamamoto and K. Maruyama, J. Chem. Soc., Chem. Commun., 1984, 904 DOI: 10.1039/C39840000904
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