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Copper(I)-Catalyzed Enantioselective Boryl Substitution of Allyl Acylals: An Efficient Approach for Enantioenriched α-Chiral γ-Acetoxyallylboronates

Yuta Takenouchi, Ryoto Kojima, Riko Momma, Hajime Ito*

*Division of Applied Chemistry and Frontier Chemistry Center, Faculty of Engineering, Hokkaido University, Sapporo, Hokkaido, 060-8628, Japan, Email:

Y. Takenouchi, R. Kojima, R. Momma, H. Ito, Synlett, 2017, 28, 270-274.

DOI: 10.1055/s-0036-1588354 (free Supporting Information)

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A copper(I)-catalyzed γ-boryl substitution of allyl acylals enables an enantioselective synthesis of α-chiral γ-acetoxyallylboronates with high E/Z selectivity and enantioselectivity. A subsequent reaction with aldehydes provides monoprotected anti-1,2-diol derivatives with high stereoselectivity.

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Key Words

boron, allylboronates, enantioselectivity, copper, catalysis, allylation

ID: J60-Y2017