Stereoselective Synthesis of 7-(E)-Arylidene-2-chloro-6-azabicyclo[3.2.1]octanes via Aluminum Chloride-Promoted Cyclization/Chlorination of Six-Membered Ring 3-Enynamides

Ming Chang P. Yeh; Yi Mei Chang; Hsin Hui Lin

doi:10.1002/adsc.201700271

Stereoselective Synthesis of 7-(E)-Arylidene-2-chloro-6-azabicyclo[3.2.1]octanes via Aluminum Chloride-Promoted Cyclization/Chlorination of Six-Membered Ring 3-Enynamides

Ming Chang P. Yeh^*, Yi Mei Chang, Hsin Hui Lin

^*Corresponding author for this work

Department of Chemistry

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

6 Citations (Scopus)

Abstract

An efficient stereoselective synthesis of 7-(E)-arylidene-2-chloro-6-azabicyclo[3.2.1]octanes is described. The aluminum chloride-promoted cyclization/chlorination of six-membered ring 3-enynamides enables a straightforward approach to the 6-azabicyclo[3.2.1]octane nucleus that is incorporated in many biologically active compounds. Acid treatment of the resultant chlorinated arylideneazabicyclooctanes furnishes 3-alkanoyl-4-chlorocyclohexanamines in excellent yields and high stereoselectivity. (Figure presented.).

Original language	English
Pages (from-to)	2196-2201
Number of pages	6
Journal	Advanced Synthesis and Catalysis
Volume	359
Issue number	13
DOIs	https://doi.org/10.1002/adsc.201700271
Publication status	Published - 2017 Jul 3

Keywords

Lewis acids
amides
amines
cyclization
diastereoselectivity
halogenation

ASJC Scopus subject areas

Catalysis
Organic Chemistry

Access to Document

10.1002/adsc.201700271

Cite this

Stereoselective Synthesis of 7-(E)-Arylidene-2-chloro-6-azabicyclo[3.2.1]octanes via Aluminum Chloride-Promoted Cyclization/Chlorination of Six-Membered Ring 3-Enynamides. / Yeh, Ming Chang P.; Chang, Yi Mei; Lin, Hsin Hui.
In: Advanced Synthesis and Catalysis, Vol. 359, No. 13, 03.07.2017, p. 2196-2201.

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

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title = "Stereoselective Synthesis of 7-(E)-Arylidene-2-chloro-6-azabicyclo[3.2.1]octanes via Aluminum Chloride-Promoted Cyclization/Chlorination of Six-Membered Ring 3-Enynamides",

abstract = "An efficient stereoselective synthesis of 7-(E)-arylidene-2-chloro-6-azabicyclo[3.2.1]octanes is described. The aluminum chloride-promoted cyclization/chlorination of six-membered ring 3-enynamides enables a straightforward approach to the 6-azabicyclo[3.2.1]octane nucleus that is incorporated in many biologically active compounds. Acid treatment of the resultant chlorinated arylideneazabicyclooctanes furnishes 3-alkanoyl-4-chlorocyclohexanamines in excellent yields and high stereoselectivity. (Figure presented.).",

keywords = "Lewis acids, amides, amines, cyclization, diastereoselectivity, halogenation",

author = "Yeh, {Ming Chang P.} and Chang, {Yi Mei} and Lin, {Hsin Hui}",

note = "Publisher Copyright: {\textcopyright} 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2017",

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doi = "10.1002/adsc.201700271",

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T1 - Stereoselective Synthesis of 7-(E)-Arylidene-2-chloro-6-azabicyclo[3.2.1]octanes via Aluminum Chloride-Promoted Cyclization/Chlorination of Six-Membered Ring 3-Enynamides

AU - Yeh, Ming Chang P.

AU - Chang, Yi Mei

AU - Lin, Hsin Hui

PY - 2017/7/3

Y1 - 2017/7/3

N2 - An efficient stereoselective synthesis of 7-(E)-arylidene-2-chloro-6-azabicyclo[3.2.1]octanes is described. The aluminum chloride-promoted cyclization/chlorination of six-membered ring 3-enynamides enables a straightforward approach to the 6-azabicyclo[3.2.1]octane nucleus that is incorporated in many biologically active compounds. Acid treatment of the resultant chlorinated arylideneazabicyclooctanes furnishes 3-alkanoyl-4-chlorocyclohexanamines in excellent yields and high stereoselectivity. (Figure presented.).

AB - An efficient stereoselective synthesis of 7-(E)-arylidene-2-chloro-6-azabicyclo[3.2.1]octanes is described. The aluminum chloride-promoted cyclization/chlorination of six-membered ring 3-enynamides enables a straightforward approach to the 6-azabicyclo[3.2.1]octane nucleus that is incorporated in many biologically active compounds. Acid treatment of the resultant chlorinated arylideneazabicyclooctanes furnishes 3-alkanoyl-4-chlorocyclohexanamines in excellent yields and high stereoselectivity. (Figure presented.).

KW - Lewis acids

KW - amides

KW - amines

KW - cyclization

KW - diastereoselectivity

KW - halogenation

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Stereoselective Synthesis of 7-(E)-Arylidene-2-chloro-6-azabicyclo[3.2.1]octanes via Aluminum Chloride-Promoted Cyclization/Chlorination of Six-Membered Ring 3-Enynamides

Abstract

Keywords

ASJC Scopus subject areas

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CCDC 1524546: Experimental Crystal Structure Determination

CCDC 1524550: Experimental Crystal Structure Determination

CCDC 1524549: Experimental Crystal Structure Determination

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Stereoselective Synthesis of 7-(E)-Arylidene-2-chloro-6-azabicyclo[3.2.1]octanes via Aluminum Chloride-Promoted Cyclization/Chlorination of Six-Membered Ring 3-Enynamides

Abstract

Keywords

ASJC Scopus subject areas

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Datasets

CCDC 1524546: Experimental Crystal Structure Determination

CCDC 1524550: Experimental Crystal Structure Determination

CCDC 1524549: Experimental Crystal Structure Determination

Cite this