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Synlett 2001; 2001(8): 1278-1280
DOI: 10.1055/s-2001-16068
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Radical Addition of Triphenylgermane to Vinyloxiranes: Its Application to Synthesis of 4-Vinyltetrahydro-2-furanones

Shinobu Tanaka* , Tomoaki Nakamura, Hideki Yorimitsu, Hiroshi Shinokubo, Seijiro Matsubara, Koichiro Oshima
  • *Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan; Fax + 81-75-753-48 63; E-mail: oshima@fm1.kuic.kyoto-u.ac.jp
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Publication Date:
31 December 2001 (online)

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Radical addition of triphenylgermane to vinyloxiranes proceeded in the presence of triethylborane to yield 4-triphenylgermyl-2-buten-1-ol derivatives in good yields. Iodo acetals, prepared by iodoetherification of vinyl ethers with the obtained allylic alcohol, underwent radical cyclization to give 2-alkoxy-4-vinyltetrahydrofurans, which were converted into 4-vinyltetrahydro-2-furanones by Jones oxidation. The cyclization involved fragmentation of β-triphenylgermyl radical.

vinyloxirane - triphenylgermane - radical addition - fragmentation - lactone