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

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 ma...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2017-07, Vol.359 (13), p.2196-2201
Main Authors: Yeh, Ming‐Chang P., Chang, Yi‐Mei, Lin, Hsin‐Hui
Format: Article
Language:English
Subjects:
Aluminum
amides
amines
Biological effects
Chlorination
cyclization
diastereoselectivity
halogenation
High temperature
Lewis acids
Nuclei
Octanes
Stereoselectivity
Synthesis
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Summary: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.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201700271