Functionalised propargyllithium reagents

Article abstract of DOI:10.1016/S0040-4020(97)10141-7

The reaction of chlorinated acetylenic ether or amines 1 with lithium and a catalytic amount of DTBB (5%), in the presence of different electrophiles [Pr(i)CHO, Bu(t)CHO, PhCHO, Me₂CO, (CH₂)₅CO, Me₃SiCl] in THF at -78 or -105°C leads, after hydrolysis with water, to the corresponding products 2. The same process applied to the previously deprotonated chloroalcohol 4a or the secondary amine 4b can be carried out in a two-step reaction giving the expected products 6 by using several electrophiles [Pr(i)CHO, Bu(t)CHO, PhCHO, Me₂CO, (CH₂)₅CO, Me₃SiCl] at -78°C.