Methyllithium, with camphor

Methylcyclohexene, from 2-methyl-cyclohexanone tosylhydrazone and methyllithium, 51,69 Methylenecyclopropanes, 50,30 Methyl iodide, with triphenyl phosphite and cyclohexanol, 51,45 with triphenyl phosphite and neopentyl alcohol, 51,44 METHYL ftrans-2-IODO-l-TETRA-LIN)CARBAMATE, 51,112 Methyl (frans-2-iodo-l-tetralin)carba-mate, with potassium hydroxide to give 1,2,3,4-tetrahydronaph-thalene(l,2)imine, 51,53 Methyllithium, with camphor tosylhydrazone to give 2-bomene, 51, 66... 

Ashby and coworkers reported in 1974 stereochemical studies on addition of lithium trimethyhnagnesate to several ketones . The reactions of 4-ferf-butylcyclohexanone with methyllithium, with dimethylmagnesium and with lithium trimethyhnagnesate in ether afforded mixtures of the corresponding axial and equatorial alcohols in ratios of 65 35, 70 30 and 69 31, respectively (equation 11). Reaction of 3,3,5-trimethylcyclohexanone with lithium trimethylmagnesate yielded exclusively the axial alcohol (equation 12). Reaction of norcamphor provided 95% of the endo alcohol and 5% of the exo alcohol (equation 13). In contrast, reaction of camphor yielded the exo alcohol with high stereoselectivity (equation 14). Among the methylmetals examined, no difference in the stereoselectivity was virtually observed. 

Camphor tosylhydrazone, with methyllithium to give 2-bor-nene, 51, 66... 

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