Stereoselective preparation of (Z)-2-(trialkylsilyloxy)-2-alkenals by retrocycloaddition reactions of 4H-4-alkyl-5-(trialkylsilyloxy)-1,3-dioxins. Useful reactants for Lewis acid catalyzed [4 + 3] cyclizations

Ronald A. Aungst, Raymond Lee Funk

Research output: Contribution to journalArticle

46 Citations (Scopus)

Abstract

(matrix presented) Retrocycloadditions of 4H-4-alkyl-5-(trialkylsilyloxy)-1,3-dioxins proceed smoothly in refluxing toluene to afford (Z)-2-(trialkylsilyloxy)-2-alkenals with complete stereoselectivity. These enals undergo Sasaki-type [4 + 3] cyclizations with dienes in the presence of Lewis acids, in many instances with excellent regio- and/or stereoselectivity.

Original languageEnglish (US)
Pages (from-to)3553-3555
Number of pages3
JournalOrganic Letters
Volume3
Issue number22
DOIs
StatePublished - Nov 1 2001

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Stereoselectivity
Lewis Acids
Dioxins
Cyclization
Toluene
dienes
toluene
preparation
acids
matrices

All Science Journal Classification (ASJC) codes

  • Molecular Medicine

Cite this

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title = "Stereoselective preparation of (Z)-2-(trialkylsilyloxy)-2-alkenals by retrocycloaddition reactions of 4H-4-alkyl-5-(trialkylsilyloxy)-1,3-dioxins. Useful reactants for Lewis acid catalyzed [4 + 3] cyclizations",
abstract = "(matrix presented) Retrocycloadditions of 4H-4-alkyl-5-(trialkylsilyloxy)-1,3-dioxins proceed smoothly in refluxing toluene to afford (Z)-2-(trialkylsilyloxy)-2-alkenals with complete stereoselectivity. These enals undergo Sasaki-type [4 + 3] cyclizations with dienes in the presence of Lewis acids, in many instances with excellent regio- and/or stereoselectivity.",
author = "Aungst, {Ronald A.} and Funk, {Raymond Lee}",
year = "2001",
month = "11",
day = "1",
doi = "10.1021/ol016668f",
language = "English (US)",
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journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
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T1 - Stereoselective preparation of (Z)-2-(trialkylsilyloxy)-2-alkenals by retrocycloaddition reactions of 4H-4-alkyl-5-(trialkylsilyloxy)-1,3-dioxins. Useful reactants for Lewis acid catalyzed [4 + 3] cyclizations

AU - Aungst, Ronald A.

AU - Funk, Raymond Lee

PY - 2001/11/1

Y1 - 2001/11/1

N2 - (matrix presented) Retrocycloadditions of 4H-4-alkyl-5-(trialkylsilyloxy)-1,3-dioxins proceed smoothly in refluxing toluene to afford (Z)-2-(trialkylsilyloxy)-2-alkenals with complete stereoselectivity. These enals undergo Sasaki-type [4 + 3] cyclizations with dienes in the presence of Lewis acids, in many instances with excellent regio- and/or stereoselectivity.

AB - (matrix presented) Retrocycloadditions of 4H-4-alkyl-5-(trialkylsilyloxy)-1,3-dioxins proceed smoothly in refluxing toluene to afford (Z)-2-(trialkylsilyloxy)-2-alkenals with complete stereoselectivity. These enals undergo Sasaki-type [4 + 3] cyclizations with dienes in the presence of Lewis acids, in many instances with excellent regio- and/or stereoselectivity.

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U2 - 10.1021/ol016668f

DO - 10.1021/ol016668f

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SP - 3553

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JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

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ER -