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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
Author(s) -
Yeh MingChang P.,
Chang YiMei,
Lin HsinHui
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201700271
Subject(s) - chemistry , stereoselectivity , ring (chemistry) , octane , chloride , organic chemistry , medicinal chemistry , catalysis
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.