Tetrahedron Letters p. 2449 - 2452 (1991)
Update date:2022-07-29
Topics:
Srebnik, Morris
(Z)-Trialkenylboranes, (R1HC=CR2)3B, easily prepared by hydroboration of the corresponding alkynes with BMS in THF, rapidly react with commercially available diethylzinc in hydrocarbon solvents, in either a 1:3 or 2:3 ratio of organoborane to organozinc, to yield an equilibrium mixture, favoring the migration of alkenyl groups from boron to zinc.Addition of an aldehyde to the 2:3 reaction mixture, in the presence of 10 molpercent N-methylpiperidine, results in the exclusive transfer of both alkenyl groups from zinc, furnishing diastereomerically pure trisubstituted double bonds in allylic alcohols in good to excellent yields.
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