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On the elucidation of the mechanism of Vinca alkaloid fluorination in superacidic medium.

Authors :
Giovanelli E
Leroux S
Moisan L
Carreyre H
Thuéry P
Buisson DA
Meddour A
Coustard JM
Thibaudeau S
Rousseau B
Nicolas M
Hellier P
Doris E
Source :
Organic letters [Org Lett] 2011 Aug 05; Vol. 13 (15), pp. 4116-9. Date of Electronic Publication: 2011 Jul 06.
Publication Year :
2011

Abstract

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.<br /> (© 2011 American Chemical Society)

Details

Language :
English
ISSN :
1523-7052
Volume :
13
Issue :
15
Database :
MEDLINE
Journal :
Organic letters
Publication Type :
Academic Journal
Accession number :
21732596
Full Text :
https://doi.org/10.1021/ol201637m