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

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Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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