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Copper(I)-Catalyzed Enantioselective Nucleophilic Borylation of Aldehydes: An Efficient Route to Enantiomerically Enriched α-Alkoxyorganoboronate Esters

Koji Kubota, Eiji Yamamoto and Hajime Ito*

*Division of Chemical Process Engineering & Frontier Chemistry Center, Graduate School of Engineering, Hokkaido University, Sapporo, Hokkaido 060-8628, Japan, Email: hajitoeng.hokudai.ac.jp

K. Kubota, E. Yamamoto, H. Ito, J. Am. Chem. Soc., 2015, 137, 420-424.

DOI: 10.1021/ja511247z (free Supporting Information)



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Abstract

In a catalytic enantioselective nucleophilic borylation, a series of aldehydes reacted with B2pin2 in the presence of a copper(I)/DTBM-SEGPHOS complex as catalyst and MeOH as a proton source to give the corresponding optically active α-alkoxyorganoboronate esters with excellent enantioselectivities. These products can readily be converted to chiral alcohol derivatives through stereospecific C-C bond forming reactions.

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Key Words

Boronates


ID: J48-Y2015