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Cascade Triple-Aldehyde Addition of 1,2,3,4-Tetrakis(pinacolatoboryl)but- 2-ene: Stereoselective Synthesis of 2,3-Bis(alkylidene)alkane-1,5-diols

Authors

  • Masaki Shimizu Prof. Dr.,

    1. Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto University Katsura, Nishikyo-ku, Kyoto 615-8510, Japan, Fax: (+81) 75-383-2445
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  • Katsuhiro Shimono Dr.,

    1. Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto University Katsura, Nishikyo-ku, Kyoto 615-8510, Japan, Fax: (+81) 75-383-2445
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  • Tamejiro Hiyama Prof. Dr.

    1. Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto University Katsura, Nishikyo-ku, Kyoto 615-8510, Japan, Fax: (+81) 75-383-2445
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Abstract

Treatment of (Z)-1,2,3,4-tetrakis(pinacolatoboryl)but-2-ene, prepared from 2,3-bis(pinacolatoboryl)buta-1,3-diene and bis(pinacolato)diboron, with three molar equivalents of aldehyde in toluene at 100 °C gave the 2,3-bis(alkylidene)alkane-1,5-anti-diol as a single stereoisomer. The reaction is applicable to both aromatic and α-unbranched aliphatic aldehydes. The 1,5-anti-diols were also synthesized by the one-pot preparation/triple-aldehyde addition of the tetraborylated butene. Experimental results for the stepwise treatment of the butene with two types of aldehydes suggest that the rate-determining step of the triple-aldehyde addition is the third allylation.

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