On the Elucidation of the Mechanism of Vinca Alkaloid Fluorination in Superacidic Medium

Detailed investigations on one of the key steps of the superacidic fluorination of Vinca alkaloids that is the origin of C20′ activation are reported. While two different pathways can be envisioned for the emergence of the transient secondary carbocationic intermediate, isotopic labeling experiments...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2011-08, Vol.13 (15), p.4116-4119
Main Authors: Giovanelli, Emerson, Leroux, Sébastien, Moisan, Lionel, Carreyre, Hélène, Thuéry, Pierre, Buisson, David-Alexandre, Meddour, Abdelkrim, Coustard, Jean-Marie, Thibaudeau, Sébastien, Rousseau, Bernard, Nicolas, Marc, Hellier, Paul, Doris, Eric
Format: Article
Language:English
Subjects:
Acids - chemistry
Dimerization
Halogenation
Hydrogen-Ion Concentration
Molecular Structure
Vinca Alkaloids - chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Detailed investigations on one of the key steps of the superacidic fluorination of Vinca alkaloids that is the origin of C20′ activation are reported. While two different pathways can be envisioned for the emergence of the transient secondary carbocationic intermediate, isotopic labeling experiments unambiguously revealed the involvement of a 1,2-hydride shift mechanism.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol201637m