I am working with N-tosyl-2-piperidone and attempts to use the lithium enolate of this compound to perform an nucleophilic acyl substitution reaction on an several chloroformate esters in THF has lead to multiple products. The major side product of this appears to be the vinyl carbonate, formed by O-attack of the enolate on the chloroformate ester.

Reaction scheme

I have used the cyanoformate analogues with success, but benzyl cyanoformate is impressively expensive and if I can avoid synthesizing it (with sodium or potassium cyanide), I would prefer to do so.

Does anyone know of a procedure for increasing the C-addition product of a reaction like this?


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