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Boron-Templated Dimerization of Allylic Alcohols To Form Protected 1,3-Diols via Acid Catalysis

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journal contribution
posted on 25.11.2019, 19:41 by S. Hadi Nazari, Kelton G. Forson, Erin E. Martinez, Nicholas J. Hansen, Kyle J. Gassaway, Nathan M. Lyons, Karissa C. Kenney, Gabriel A. Valdivia-Berroeta, Stacey J. Smith, David J. Michaelis
We report an unprecedented boron-templated dimerization of allylic alcohols that generates a 1,3-diol product with two stereogenic centers in high yield and diastereoselectivity. This acid-catalyzed reaction is achieved via in situ formation of a boronic ester intermediate that facilitates selective cyclization and formation of a cyclic boronic ester product. High yields are observed with a variety of allylic alcohols, and mechanistic studies confirm the role of boron as a template for the reaction.