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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: zhouyusimm.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 (free Supporting Information)


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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

indoles


ID: J42-Y2017