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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

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 straight forward approach to the 6‐azabicyclo[3.2.1]octane nucleus incorporated in many biologically active compounds. Acid treatment of the resultant chlorinated arylideneazabicycles furnishes 3‐alkanoyl‐4‐chlorocyclohexanamines in excellent yields and high stereoselectivity.

Authors:   Ming-Chang Yeh, Yi-Mei Chang, Hsin-Hui Lin
Journal:   Advanced Synthesis & Catalysis
Year:   2017
Pages:   n/a
DOI:   10.1002/adsc.201700271
Publication date:   30-Mar-2017
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