Yb(NTf2)3-catalyzed [3 + 3] cycloaddition between isatin ketonitrones and cyclopropanes to construct novel spiro[tetrahydro-1,2-oxazine]oxindoles

Hai-Bin Yang; Min Shi

doi:10.1039/C2OB26413G

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Yb(NTf₂)₃-catalyzed [3 + 3] cycloaddition between isatin ketonitrones and cyclopropanes to construct novel spiro[tetrahydro-1,2-oxazine]oxindoles†

Hai-Bin Yang^a and Min Shi*^a

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* Corresponding authors

^a State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P.R. China
E-mail: mshi@mail.sioc.ac.cn

Abstract

Yb(NTf₂)₃-catalyzed [3 + 3] cycloaddition between isatin ketonitrones and cyclopropanes is described. A variety of spiro[tetrahydro-1,2-oxazine]oxindoles were obtained in moderate to good yields along with good regioselectivities. This is the first example of the intermolecular [3 + 3] cycloaddition between ketone-derived nitrones and cyclopropanes.

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Article information

DOI: https://doi.org/10.1039/C2OB26413G
Article type: Paper
Submitted: 20 Jul 2012
Accepted: 29 Aug 2012
First published: 31 Aug 2012

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Org. Biomol. Chem., 2012,10, 8236-8243

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Yb(NTf₂)₃-catalyzed [3 + 3] cycloaddition between isatin ketonitrones and cyclopropanes to construct novel spiro[tetrahydro-1,2-oxazine]oxindoles

H. Yang and M. Shi, Org. Biomol. Chem., 2012, 10, 8236 DOI: 10.1039/C2OB26413G

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Organic & Biomolecular Chemistry