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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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Type
research article
DOI
10.1002/(SICI)1099-0690(199902)1999:2%3C459::AID-EJOC459%3E3.0.CO;2-F
Author(s)
Schlosser, Manfred  
Kotthaus, Martina
Date Issued

1999

Published in
European Journal of Organic Chemistry
Issue

2

Start page

459

End page

462

Subjects

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)

Editorial or Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LSCO  
Available on Infoscience
March 3, 2006
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/226967
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