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Paper | Regular issue | Vol 32, No. 9, 1991, pp.1757-1764
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5775
Diastereoselectivity in the Reaction of 3-Methyl-5-(methyl- or phenyl)isoxazol-4-yllithium and α,α’-Dimethylcycloalkanones

Cecilia Polo, Vicente Ramos, Tomás Torroba,* Matías L. Rodoríguez, Ricardo Bossio, Stefano Marcaccini, and Roberto Pepino

*Departmento de Quimica Orgánica. Facultd de Veter inaria, Universidad de Extremadura, 10071 Cáceres, Spain.

Abstract

Addition of 3-methyl-4-lithio-5-(methyl- or phenyl)isoxazoles to stereoisomeric mixures of α,α’-dimethylcycloalkanones afforded meso 1S*,2R*,(5 or 6)S*-2,(5 or 6)-dimethyl-1-[3’-methyl-5’-(methyl- or phenyl)isoxazol-4’-yl]cycloalkan-1-ols. In one case none of meso form, but only the racemic 2,6-dimethyl-1-(3’-methyl-5’-phenylisoxazol-4’-yl)cyclohexan-1-ol was obtained. This compound showed restricted rotation phenomena at room temperature.