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

doi:10.1055/s-1991-20891

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 journal › Article › peer-review

28 Scopus citations

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 language	English (US)
Pages (from-to)	823-824
Number of pages	2
Journal	Synlett
Volume	1991
Issue number	11
DOIs	https://doi.org/10.1055/s-1991-20891
State	Published - Nov 1991
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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10.1055/s-1991-20891

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

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.",

author = "Isao Kadota and Vladimir Gevorgyan and Yamada, {Juan Ichi} and Yoshinori Yamamoto",

year = "1991",

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doi = "10.1055/s-1991-20891",

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T1 - Synthesis of β-alkoxycyclic ethers from ω-organometallic ether acetalsstereocontrol with the combined lewis acid system, titanium(IV) chloride-triphenylphosphine

AU - Kadota, Isao

AU - Gevorgyan, Vladimir

AU - Yamada, Juan Ichi

AU - Yamamoto, Yoshinori

PY - 1991/11

Y1 - 1991/11

N2 - 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.

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

Abstract

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