ISSN:
1434-193X
Keywords:
Electrophilic substitution
;
Metalations
;
Monoterpene
;
Protective groups
;
Superbase
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
-When treated with butyllithium and potassium tert-butoxide for 2 h at 0 °C in hexanes, the unsaturated monoterpenic alcohol isopulegol is simultaneously deprotonated at the hydroxy function and the allylic methyl 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, alcohols being instantaneously converted by superbases into alcoholates.
Type of Medium:
Electronic Resource
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