A study of methyl and tert-butyl as non migrating groups in the reaction of me(organyl)zinc and t-bu(organyl)zinc with aldehydes

Article abstract of DOI:10.1016/S0040-4039(00)77253-4

A series of mixed methyl (organyl) and tert-butyl(organyl)zincs were prepared by reaction of ZnCl₂ with Grignard reagents. In the presence of salts t-butyl migrates to a lessor extent than methyl in the reaction with aldehydes. In the absence of salts both groups are comparable. BuZnMe prepared under salt-free conditions adds to benzaldehyde in 82.4% ee and in 85% yield, comparable to the reaction with distilled dibutylzinc.