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Synlett 1991; 1991(11): 823-824
DOI: 10.1055/s-1991-20891
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Synthesis of β-Alkoxycyclic Ethers from ω-Organometallic Ether Acetals. Stereocontrol with the Combined Lewis Acid System, Titanium(IV) Chloride-Triphenylphosphine

Isao Kadota* , Vladimir Gevorgyan, Juan-ichi Yamada, Yoshinori Yamamoto
  • *Department of Chemistry, Faculty of Science, Tohoku University, Sendai 980, Japan
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Publication Date:
07 March 2002 (online)

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The titanium(IV) chloride-triphenylphosphine mediated intramolecular cyclization of γ-oxo-substituted allylic silane 1 (4-[3-(trimethylsilyl)-1- propenyloxy]butanal propylene acetal) having an acetal group at the terminus of the carbon chain produced the 6-membered trans isomer 2a [trans-3-(3-hydroxypropoxy)-2-vinyltetrahydropyran] with very high diastereoselectivity in high yield. Highly stereoselective synthesis of seven- and eight-membered rings was also accomplished by the use of titanium(IV) chloride-triphenylphosphine.

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