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Regio- and Stereoselective Synthesis of Multi-Alkylated Allylic Boronates through Three-Component Coupling Reactions between Allenes, Alkyl Halides, and a Diboron Reagent

Yu Ozawa, Kohei Endo and Hajime Ito*

*Institute for Chemical Reaction Design and Discovery (WPI-ICReDD), Hokkaido University, Sapporo, Hokkaido 060-8628, Japan, Email:

Y. Ozawa, K. Endo, H. Ito, J. Am. Chem. Soc., 2021, 143, 13865-138772.

DOI: 10.1021/jacs.1c06538

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A copper(I)-catalyzed regio- and stereoselective three-component coupling reactions between gem-dialkylallenes, alkyl halides, and bis(pinacolato)diboron provides sterically congested allylic boronates. A subsequent allylboration of aldehydes diastereoselectively furnished the corresponding homoallylic alcohols that bear a quaternary carbon.

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Key Words

allylic boronates, multicomponent reactions, alkenes

ID: J48-Y2021