The areas of carbonyl borylation and the homologation of carbon-boron bonds have provided a number of fruitful methods in organic synthesis. Combining these approaches, the homologation of α-oxyboronate esters, provides pathways to access complex organoboronate esters stereoselectively. To this end, the homologation of α-silyloxyboronate esters with lithiated allyl chlorides to form β-silyloxy allylboronate esters is reported. Direct oxidation of the homologation products provides β-silyloxy allyl alcohols in good yield. The homologation provides a range of allylic alcohols, albeit with low diastereoselectivity.
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| http://dx.doi.org/10.1016/j.tetlet.2020.152082 | DOI Listing |
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