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

Research output: Contribution to journalArticle

2 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 languageEnglish
Pages (from-to)2196-2201
Number of pages6
JournalAdvanced Synthesis and Catalysis
Volume359
Issue number13
DOIs
Publication statusPublished - 2017 Jan 1

Fingerprint

Aluminum chloride
Stereoselectivity
Chlorination
Cyclization
Acids
6-azabicyclo(3.2.1)octane
aluminum chloride

Keywords

  • Lewis acids
  • amides
  • amines
  • cyclization
  • diastereoselectivity
  • halogenation

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

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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}",
year = "2017",
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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 - 2017/1/1

Y1 - 2017/1/1

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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