Enantioselective Organocatalytic α-Fluorination of Cyclic Ketones
Journal of the American Chemical SocietyPublished 19 January 2011
Piotr Kwiatkowski, T. D. Beeson, Jay C. Conrad, David W. C. MacMillan
Citations230
SJR quartileQ1
SJR score5.55
SNIP2.61
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TL;DR
The first highly enantioselective α-fluorination of ketones using organocatalysis has been accomplished via high-throughput evaluation of a new library of amine catalysts, and the optimal system, a primary amine functionalized Cinchona alkaloid, allows the direct and asymmetric α- fluidination of a variety of carbo- and heterocyclic substrates.
Abstract
The first highly enantioselective α-fluorination of ketones using organocatalysis has been accomplished. The long-standing problem of enantioselective ketone α-fluorination via enamine activation has been overcome via high-throughput evaluation of a new library of amine catalysts. The optimal system, a primary amine functionalized Cinchona alkaloid, allows the direct and asymmetric α-fluorination of a variety of carbo- and heterocyclic substrates. Furthermore, this protocol also provides diastereo-, regio-, and chemoselective catalyst control in fluorinations involving complex carbonyl systems.
Keywords
ChemistryPharmacology, Toxicology and Pharmaceutics
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