Rh(III)-Catalyzed C-H Cyclization of Arylnitrones with Diazo Compounds: Access to 3-Carboxylate Substituted N-Hydroxyindoles
Yazhou Li, Jian Li, Xiaowei Wu, Yu Zhou* and Hong Liu*
*CAS Key Laboratory of Receptor Research, Shanghai Institute
of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Shanghai
201203, China, Email: zhouyu
simm.ac.cn, hliusimm.ac.cn
Y. Li, J. Li, X. Wu, Y. Zhou, H. Liu, J. Org. Chem., 2017, 82, 8984-8994.
DOI: 10.1021/acs.joc.7b01393
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Abstract
N-hydroxyindole derivatives offer an unique structural motif and various biological activities. A Rh(III)-catalyzed reaction of arylnitrones with α-diazoketoesters or α-diazodiketones provides N-hydroxyindole derivatives. The N-hydroxyindole scaffold is built by blocking the cleavage of the N-O bond selectively, while eliminating the acyl group of α-diazoketoesters or α-diazodiketones preferentially.
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proposed mechanism
Key Words
ID: J42-Y2017
