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

• Published in: European Journal of Organic Chemistry, num. 2, p. 459-462
• Publication date: 1999

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)]

Keywords: Metalation; Substitution reaction (metalation and substitution of allylic position in isopulegol in presence of unprotected hydroxy function) ; isopulegol electrophilic substitution metalation

Note:

CAN 130:153807 30-10 Terpenes and Terpenoids Inst. Chimie Organique, Sec. Chimie,Univ. Lausanne,Lausanne,Switz. Journal 1434-193X written in English. 89-79-2 (Isopulegol) Role: RCT (Reactant), RACT (Reactant or reagent) (metalation and substitution of allylic position in isopulegol in presence of unprotected hydroxy function); 13834-14-5P; 110328-55-7P; 110328-56-8P; 220314-64-7P; 220314-66-9P; 220314-67-0P; 220314-69-2P; 220314-70-5P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (metalation and substitution of allylic position in isopulegol in presence of unprotected hydroxy function); 38049-01-3P; 38049-03-5P; 203584-73-0P; 220314-63-6P; 220314-68-1P Role: SPN (Synthetic preparation), PREP (Preparation) (metalation and substitution of allylic position in isopulegol in presence of unprotected hydroxy function)

Reference

• LSCO-ARTICLE-1999-004

Record created on 2006-03-03, modified on 2016-08-08