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Synlett 1998; 1998(10): 1150-1152
DOI: 10.1055/s-1998-1888
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Stereoselective Synthesis of 2,3,5-Substituted Tetrahydrofurans by Silicon-Directed Cyclization of Allylsilanes Bearing a Hydroxy Moiety

Takahiko Akiyama* , Yuhsuke Ishida
  • *Department of Chemistry, Faculty of Science, Gakushuin University, 1-5-1, Mejiro, Toshima-ku, Tokyo 171-8588, Japan; Fax + 81-3-5992-1029; E-mail: takahiko.akiyama@gakushuin.ac.jp
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Publication Date:
31 December 2000 (online)

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Acid promoted cyclization of bishomoallylic alcohols bearing allylsilanes proceeded smoothly by way of β-silyl carbocation intermediate to furnish tetrahydrofurans highly stereoselectively.

allylsilane - tetrahydrofuran - cyclization - β-silyl carbocation

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