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J Am Chem Soc. 2010 Jun 2;132(21):7266-7. doi: 10.1021/ja1027327.

Copper-catalyzed synthesis of azaspirocyclohexadienones from alpha-azido-N-arylamides under an oxygen atmosphere.

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Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore.


A copper-catalyzed reaction of alpha-azido-N-arylamides was found to proceed under an oxygen atmosphere to afford azaspirocyclohexadienones. The present transformation is carried out by a sequence of denitrogenative formation of iminyl copper species from alpha-azido-N-arylamides and their imino-cupration with an intramolecular benzene ring on the amido nitrogen followed by consecutive formation of C=O bonds. The preliminary investigation revealed that molecular oxygen is a prerequisite for achieving the present catalytic cyclization and that one of the oxygen atoms of O(2) was found to be incorporated into the cyclohexadienone moiety.

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