Templated organic transformations are gaining popularity in synthetic chemistry because they allow for the synthesis of complex molecules that may be difficult to produce using traditional methodologies. Templated reactions typically achieve high yield and selectivity through the preorganization of reacting substrates in close proximity. One current strategy that employs the preorganization of substrates includes the use of removable covalent tethers. Through an NSF-REU program at Brigham Young University, we discovered a selective acid-catalyzed dimerization of simple allylic alcohols that employs a boronic acid tether to achieve high regio- and diastereoselectivity. This process proceeds via <i>in situ</i> formation of a boronic ester with two allylic alcohols and results in the production of a boron-protected 1,3-diol product. After extensive optimization, these boron-protected diols were generated with high yield and diastereoselectivity from a range of different allylic alcohol substrates. Derivatization studies on the boron-protected 1,3-diol product also demonstrate the synthetic utility of this new process.

Boron-templated dimerization of allylic alcohols to form protected 1,3-diols via acid catalysis

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.