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  4. Isopulegol as a model compound. Metalation and substitution of an allylic position in the presence of an unprotected hydroxy function
 
research article

Isopulegol as a model compound. Metalation and substitution of an allylic position in the presence of an unprotected hydroxy function

Schlosser, Manfred  
•
Kotthaus, Martina
1999
European Journal of Organic Chemistry

When treated with BuLi and KOCMe3 for 2 h at 0 Deg in hexane, the unsatd. monoterpenic alc. isopulegol is simultaneously deprotonated at the hydroxy function and the allylic Me group. The metaloxy allylmetal species thus generated can be silylated, alkylated, carboxylated, and oxidized to afford the expected products in good to excellent yields. Thus, a specific protection of hydroxy groups is not required, alcs. being instantaneously converted by superbases into alcoholates. [on SciFinder (R)]

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