Synthesis of β-alkoxycyclic ethers from ω-organometallic ether acetalsstereocontrol with the combined lewis acid system, titanium(IV) chloride-triphenylphosphine

Isao Kadota, Vladimir Gevorgyan, Juan Ichi Yamada, Yoshinori Yamamoto

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)823-824
Number of pages2
JournalSynlett
Volume1991
Issue number11
DOIs
Publication statusPublished - Nov 1 1991
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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