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

^*此作品的通信作者

化學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

6 引文斯高帕斯（Scopus）

摘要

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.).

原文	英語
頁（從 - 到）	2196-2201
頁數	6
期刊	Advanced Synthesis and Catalysis
卷	359
發行號	13
DOIs	https://doi.org/10.1002/adsc.201700271
出版狀態	已發佈 - 2017 7月 3

ASJC Scopus subject areas

催化
有機化學

存取文件

10.1002/adsc.201700271

其它文件與鏈接

CCDC 1524546: Experimental Crystal Structure Determination
Yeh, M. P. (Creator), Chang, Y. (Creator) & Lin, H. (Creator), Unknown Publisher, 2017
DOI: 10.5517/ccdc.csd.cc1n5dx4, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1n5dx4&sid=DataCite
資料集: Dataset
CCDC 1524550: Experimental Crystal Structure Determination
Yeh, M. P. (Creator), Chang, Y. (Creator) & Lin, H. (Creator), Unknown Publisher, 2017
DOI: 10.5517/ccdc.csd.cc1n5f19, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1n5f19&sid=DataCite
資料集: Dataset
CCDC 1524549: Experimental Crystal Structure Determination
Yeh, M. P. (Creator), Chang, Y. (Creator) & Lin, H. (Creator), Unknown Publisher, 2017
DOI: 10.5517/ccdc.csd.cc1n5f08, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1n5f08&sid=DataCite
資料集: Dataset

引用此

@article{4555d0a1c76e4684b8935cfcb583002f,

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",

month = jul,

day = "3",

doi = "10.1002/adsc.201700271",

language = "English",

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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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JO - Advanced Synthesis and Catalysis

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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

摘要

ASJC Scopus subject areas

存取文件

其它文件與鏈接

指紋

資料集

CCDC 1524546: Experimental Crystal Structure Determination

CCDC 1524550: Experimental Crystal Structure Determination

CCDC 1524549: Experimental Crystal Structure Determination

引用此