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Substituent Enabled Divergent Synthesis of N‐Heterocycles: a Metal Carbene Approach Involving Intramolecular Carbene Interception
Author(s) -
Xu HuaDong,
Xu Ke,
Jia ZhiHong,
Zhou Hao,
Jiang Pan,
Lu XiaoLong,
Pan YingPeng,
Wu Hao,
Ding Yun,
Shen MeiHua,
Pan XianHua
Publication year - 2014
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201402151
Subject(s) - chemistry , carbene , substituent , intramolecular force , sulfonyl , aryl , rhodium , imine , medicinal chemistry , hydrolysis , combinatorial chemistry , catalysis , stereochemistry , organic chemistry , alkyl
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.