Nickel-Catalyzed 1,4-Addition of Trialkylboranes to α,β-Unsaturated Esters: Dramatic Enhancement by Addition of Methanol

Koji Hirano, Hideki Yorimitsu* and Koichiro Oshima*

*Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto-daigaku Katsura, Nishikyo-ku, Kyoto 615-8510, Japan, Email: oshimaorgrxn.mbox.media.kyoto-u.ac.jp, yoriorgrxn.mbox.media.kyoto-u.ac.jp

K. Hirano, H. Yorimitsu, K. Oshima, Org. Lett., 2007, 9, 1541-1544.

DOI: 10.1021/ol070288y

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Abstract

A nickel catalyst system for 1,4-addition of trialkylboranes to α,β-unsaturated esters has been developed. For the alkylation reaction with 9-alkyl-9-BBNs, addition of methanol was found to be essential.

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Key Words

Hydroboration, 1,4-Addition

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ID: J54-Y2007-1150