Tetrahedron p. 17201 - 17210 (1997)
Update date:2022-08-03
Topics:
Gomez, Cecilia
Huerta, Fernando F.
Pastor, Isidro M.
Yus, Miguel
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.
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