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Substituent Enabled Divergent Synthesis Of N‐Heterocycles: A Metal Carbene Approach Involving Intramolecular Carbene Interception

Hua-Dong Xu, Ke Xu, Zhi‐Hong Jia, Hao Zhou, Pan Pan Jiang, Xiao-long Lu, Ying-Peng Pan, Hao Wu, Yun Ding, Mei-Hua Shen, Xian‐Hua Pan
Published 2014 · Chemistry
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N-Aryl-N-allyl-bis-functionalized amino-1-sulfonyl-1,2,3-trizoles undergo rhodium-catalyzed cyclization reactions and subsequent hydrolytic cleavage of the sulfonyl imine to give two structurally distinct N-heterocycles, 3-indolyl aldehydes and 3-azabicyclo[3,1,0]hexyl aldehydes. The product ratio can be tuned by varying the electronic properties of the two functional groups attached to the N atom. Based on these findings, two efficient and general methods for the synthesis of highly valuable 3-indolyl aldehydes and 3-azabicyclo[3,1,0]hexyl aldehydes have been developed.

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