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Issue 60, 2013
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Enantioselective 1,3-dipolar cycloaddition of methyleneindolinones and N,N′-cyclic azomethine imines

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Abstract

A new chiral bis-phosphoric acid 3l bearing triple axial chirality was synthesized and applied to effect a highly enantioselective 1,3-dipolar cycloaddition reaction between N,N′-azomethine imines and methyleneindolinones for the creation of chiral spiro[pyrazolidin-3,3′-oxindoles] in excellent yields and selectivities. MS experiment and DFT calculation studies prompted us to propose a dual H-bond donor activation mode of bis-phosphoric acid which is different from the traditional phosphoric acid catalysis.

Graphical abstract: Enantioselective 1,3-dipolar cycloaddition of methyleneindolinones and N,N′-cyclic azomethine imines

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Publication details

The article was received on 27 Feb 2013, accepted on 15 Apr 2013 and first published on 16 Apr 2013


Article type: Communication
DOI: 10.1039/C3CC41507D
Citation: Chem. Commun., 2013,49, 6713-6715
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    Enantioselective 1,3-dipolar cycloaddition of methyleneindolinones and N,N′-cyclic azomethine imines

    L. Hong, M. Kai, C. Wu, W. Sun, G. Zhu, G. Li, X. Yao and R. Wang, Chem. Commun., 2013, 49, 6713
    DOI: 10.1039/C3CC41507D

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