Abstract
(Z)-Trialkenylboranes, (R 1HC=CR 2) 3B, easily prepared by hydroboration of the corresponding alkynes with BMS in THF, rapidly react with commercially available diethylzinc in hydrocarbon solvents, in eithe a 1:3 or 2:3 ratio of or ganoborane 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 mol % N-methylpiperidine, results in the exclusive transfer of both alkenyl groups from zinc, furnishing diastereomerically pure trisubstituted double bnds in allylic alcohols in good to excellent yields.
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