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 L. Funk

doi:10.1021/ol016668f

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 L. Funk

Chemistry

Research output: Contribution to journal › Article › peer-review

54 Scopus citations

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 language	English (US)
Pages (from-to)	3553-3555
Number of pages	3
Journal	Organic Letters
Volume	3
Issue number	22
DOIs	https://doi.org/10.1021/ol016668f
State	Published - Nov 1 2001

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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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 L.\}",

year = "2001",

month = nov,

day = "1",

doi = "10.1021/ol016668f",

language = "English (US)",

volume = "3",

pages = "3553--3555",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "22",

}

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. / Aungst, Ronald A.; Funk, Raymond L.
In: Organic Letters, Vol. 3, No. 22, 01.11.2001, p. 3553-3555.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

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 L.

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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UR - https://www.scopus.com/pages/publications/0035511672#tab=citedBy

U2 - 10.1021/ol016668f

DO - 10.1021/ol016668f

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SN - 1523-7060

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EP - 3555

JO - Organic Letters

JF - Organic Letters

IS - 22

ER -

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

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