Functionalization of a non activated C-H bond: Fluorination of vindoline at C-20 in superacids

被引：14
|
作者：
Berrier, C
Jacquesy, JC
Jouannetaud, MP
Lafitte, C
Vidal, Y
Zunino, F
Fahy, J
Duflos, A
机构：
[1] Univ Poitiers, Lab Synth & Reactiv Substances Nat, UMR 6514, F-86022 Poitiers, France
[2] Ctr Rech Pierre Fabre, Div Chim Med 5, F-81106 Castres, France
来源：
TETRAHEDRON | 1998年 / 54卷 / 45期
关键词：
D O I：
10.1016/S0040-4020(98)00845-X
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Reaction of vindoline 1a with NBS, NCS, H2O2 in HF-SbF5 yields 7 beta substituted (Br, Cl or OH)-20-fluoro-6,7-dihydrovindolines. These results imply reaction of the electrophile (Br+, Cl+ and OH+ equivalent) on the beta-face of C-6-C-7 double bond to give oniums ions, followed by a 1,3-hydride shift from C-20 to Cd, and fluorination of the resulting ion. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：13761 / 13770
页数：10
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