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Isopulegol as a Model Compound: Metalation and Substitution of an Allylic Position in the Presence of an Unprotected Hydroxy Function
Author(s) -
Schlosser Manfred,
Kotthaus Martina
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199902)1999:2<459::aid-ejoc459>3.0.co;2-f
Subject(s) - chemistry , allylic rearrangement , deprotonation , metalation , alcohol , butyllithium , substitution (logic) , substitution reaction , organic chemistry , potassium , alkylation , medicinal chemistry , catalysis , ion , computer science , programming language
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.