Triflates reaction with organocuprates

Coupling with enol esters (7, 93). A new synthesis of an alkyl-substituted alkene involves coupling of a lithium dialkyl cuprate with an enol triflate,1 available from a ketone by reaction with triflic anhydride and 2,6-di-t-butylpyridine.2 A wide variety of organocuprates can be used and the geometry of the enolate is largely retained. Reported yields are in the range 60 100%. 

Substituted 1,2,3,4-tetrahydropyridines. Enol triflates are readily prepared from V-alkoxycarbonyl-2-piperidones by successive treatment with LHMDS and reagent (1). The triflyloxy group can be replaced on reaction with organocuprates and carbonylation the product from the latter reaction is a precursor of pipecolic acid. 

The McMurry-Scott cross coupling reaction22 between enol triflates and organocuprates generally proceeds with retention of the configuration in the parent enol triflate component. In these reactions it is widely assumed that a planar alkenylcopper(III) intermediate is formed by oxidative... 

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