Efficient synthesis of isochromanones and isoquinolinesviaYb(OTf)3-catalyzed tandem oxirane/aziridine ring opening/Friedel–Crafts cyclization

Lai Wei; Junliang Zhang

doi:10.1039/C2CC17836B

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Efficient synthesis of isochromanones and isoquinolinesviaYb(OTf)₃-catalyzed tandem oxirane/aziridine ring opening/Friedel–Crafts cyclization†

Lai Wei^a and Junliang Zhang*^ab

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* Corresponding authors

^a Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 N, Zhongshan Road, Shanghai 200062, P. R. China
E-mail: jlzhang@chem.ecnu.edu.cn
Fax: +86 21-6223-3213

^b State key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, P. R. China

Abstract

The first example of Yb(OTf)₃-catalyzed tandem ring opening/Friedel–Crafts cyclization of oxiranyl and aziridinyl ketonesvia selective C–C bond cleavage under mild conditions was developed. Isochromanones and isoquinolines are formed in reasonable yields, which often serve as building blocks for complex chemical synthesis.

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Article information

DOI: https://doi.org/10.1039/C2CC17836B
Article type: Communication
Submitted: 14 Dec 2011
Accepted: 17 Jan 2012
First published: 18 Jan 2012

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Chem. Commun., 2012,48, 2636-2638

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Efficient synthesis of isochromanones and isoquinolinesviaYb(OTf)₃-catalyzed tandem oxirane/aziridine ring opening/Friedel–Crafts cyclization

L. Wei and J. Zhang, Chem. Commun., 2012, 48, 2636 DOI: 10.1039/C2CC17836B

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