Design, synthesis, and evaluation of a novel class of enantioselective electrophilic fluorinating agents:: N-fluoro ammonium salts of cinchona alkaloids (F-CA-BF4)

被引：168

作者：

Cahard, D

Audouard, C

Plaquevent, JC

Roques, N

机构：

[1] Univ Rouen, IRCOF, UPRESA 6014, F-76821 Mt St Aignan, France

[2] Rhodia Rech, F-69192 St Fons, France

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 23期

关键词：

D O I：

10.1021/ol006610l

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The first enantiopure N-fluoro quaternary ammonium salts of cinchona alkaloids as enantioselective fluorinating agents are reported. A one step transfer-fluorination on the naturally occurring cinchona alkaloids gave the fluorinating agents F-CA BF4. This new generation of fluorinating agents exhibited asymmetric induction up to 61% on fluorination of enolates and silyl enol ethers of 2-methyl-1-tetralone.

引用

页码：3699 / 3701

页数：3

共 8 条

[1] N-HALOGENO COMPOUNDS .14. TRANSFER FLUORINATION OF QUINUCLIDINE USING F-TEDA-BF4 (SELECTOR(TM) REAGENT) - LABORATORY SYNTHESIS OF N-FLUOROQUINUCLIDINIUM SALTS NOT REQUIRING THE USE OF ELEMENTAL FLUORINE [J].