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Design, Synthesis, and Evaluation of a Novel Class of Enantioselective Electrophilic Fluorinating Agents:  N-Fluoro Ammonium Salts of cinchona Alkaloids (F-CA-BF<INF>4</INF>)

Authors :
Cahard, D.
Audouard, C.
Plaquevent, J.-C.
Roques, N.
Source :
Organic Letters; November 2000, Vol. 2 Issue: 23 p3699-3701, 3p
Publication Year :
2000

Abstract

&lt;UFIGR ID=&quot;ol006610ln00001&quot;&gt;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-BF&lt;INF&gt;4&lt;/INF&gt;. 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.

Details

Language :
English
ISSN :
15237060 and 15237052
Volume :
2
Issue :
23
Database :
Supplemental Index
Journal :
Organic Letters
Publication Type :
Periodical
Accession number :
ejs1160646