Publication

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

Manfred Schlosser
1999
Journal Articles

Abstract

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)]

Official source

https://infoscience.epfl.ch/entities/publication/f8eade78-6e6e-4c48-880f-1095accff69d

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Manfred Schlosser
1999
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/f8eade78-6e6e-4c48-880f-1095accff69d

About this result

Related concepts (32)

Group action

In mathematics, a group action on a space is a group homomorphism of a given group into the group of transformations of the space. Similarly, a group action on a mathematical structure is a group homomorphism of a group into the automorphism group of the structure. It is said that the group acts on the space or structure. If a group acts on a structure, it will usually also act on objects built from that structure. For example, the group of Euclidean isometries acts on Euclidean space and also on the figures drawn in it.

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Related publications (1)

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

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