Reactions of Vinyloxyboranes with Carbonyl Compounds, Nitriles, and Formates

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Abstract
A new vinyloxyborane derivative, Id, was found to be formed in reaction of phenyl di-n-butylthioboronite (II) with methyl vinyl ketone. In order to explore its utilization in organic synthesis, the reactivity of Id and other known vinyloxyboranes was variously examined. Id and Ie gave β-hydroxyketones (IVa–c, Va–d) in fairly good yields when they were allowed to react with carbonyl compounds. The reaction of Ia′ and Ib with nitriles, followed by hydrolysis, afforded β-iminothioates (VIa–c) and β-ketoesters (VIIa–d) respectively. It was also found that the borane (Ib) reacted with formates or formamides at room temperature to give ethyl α-formylhexanoate.