Hydroboration of Vinyl Ethers with Diisopinocampheylborane

Article abstract of DOI:10.1021/jo00244a013

The reactions of diisopinocampheylborane with cyclic vinyl ethers having an exocyclic oxygen and with acyclic vinyl ethers having groups of varying size attached to oxygen were explored.Evidence of some interaction of the bulkier vinyl ethers with diisopinocampheylborane was obtained, but high enantiomeric excesses were not found.However, the hydroboration-oxidation of benzyl or diphenylmethyl vinyl ethers, followed by cleavage, is a practical route to partially resolved diols.