Efficient construction of benzohydrindenones from aryltrienones via domino Nazarov electrocyclization - Electrophilic aromatic substitution

Cindy C. Browder; Fredrik P. Marmsäter; F. G. West

doi:10.1139/v03-203

Efficient construction of benzohydrindenones from aryltrienones via domino Nazarov electrocyclization - Electrophilic aromatic substitution

Cindy C. Browder, Fredrik P. Marmsäter, F. G. West

Chemistry and Biochemistry

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

28 Scopus citations

Abstract

1,4-Dien-3-ones substituted with pendant arylethyl side chains attached at C-1 were readily prepared from substituted dihydrocinnamaldehydes. Treatment with TiCl₄ at low temperature effected domino Nazarov electrocyclization - arene trapping within 5 min to give racemic benzohydrindenones in near-quantitative yield and with complete diastereoselectivity.

Original language	English (US)
Pages (from-to)	375-385
Number of pages	11
Journal	Canadian Journal of Chemistry
Volume	82
Issue number	2
DOIs	https://doi.org/10.1139/v03-203
State	Published - Feb 2004

Keywords

Domino process
Electrophilic aromatic substitution
Lewis acid
Nazarov cyclization

ASJC Scopus subject areas

Catalysis
General Chemistry
Organic Chemistry

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10.1139/v03-203

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title = "Efficient construction of benzohydrindenones from aryltrienones via domino Nazarov electrocyclization - Electrophilic aromatic substitution",

abstract = "1,4-Dien-3-ones substituted with pendant arylethyl side chains attached at C-1 were readily prepared from substituted dihydrocinnamaldehydes. Treatment with TiCl4 at low temperature effected domino Nazarov electrocyclization - arene trapping within 5 min to give racemic benzohydrindenones in near-quantitative yield and with complete diastereoselectivity.",

keywords = "Domino process, Electrophilic aromatic substitution, Lewis acid, Nazarov cyclization",

author = "Browder, {Cindy C.} and Marms{\"a}ter, {Fredrik P.} and West, {F. G.}",

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language = "English (US)",

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pages = "375--385",

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AU - Marmsäter, Fredrik P.

AU - West, F. G.

PY - 2004/2

Y1 - 2004/2

N2 - 1,4-Dien-3-ones substituted with pendant arylethyl side chains attached at C-1 were readily prepared from substituted dihydrocinnamaldehydes. Treatment with TiCl4 at low temperature effected domino Nazarov electrocyclization - arene trapping within 5 min to give racemic benzohydrindenones in near-quantitative yield and with complete diastereoselectivity.

AB - 1,4-Dien-3-ones substituted with pendant arylethyl side chains attached at C-1 were readily prepared from substituted dihydrocinnamaldehydes. Treatment with TiCl4 at low temperature effected domino Nazarov electrocyclization - arene trapping within 5 min to give racemic benzohydrindenones in near-quantitative yield and with complete diastereoselectivity.

KW - Domino process

KW - Electrophilic aromatic substitution

KW - Lewis acid

KW - Nazarov cyclization

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JF - Canadian Journal of Chemistry

IS - 2

ER -

Efficient construction of benzohydrindenones from aryltrienones via domino Nazarov electrocyclization - Electrophilic aromatic substitution

Abstract

Keywords

ASJC Scopus subject areas

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