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Boron-Templated Dimerization of Allylic Alcohols To Form Protected 1,3-Diols via Acid Catalysis
S Hadi Nazari1, Kelton G Forson1, Erin E Martinez1
1Brigham Young University , Provo , Utah 84602 , United States.
Abstract:
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.
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