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Synthesis and regiochemistry of spiro indane-1,3-dione compounds

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Abstract

Spiro indane-1,3-dione compounds have been synthesized by 1,3-dipolar cycloaddition of ninhydrin, l-proline, and an alkene (either a chalcone or an (E)-β-arylnitrostyrene). All these reactions proceed with good yield and with high regioselectivity and stereoselectivity. The structures were studied by NMR spectroscopy, MS, and X-ray diffraction analysis. It was found that these two kinds of alkene lead to different regioselectivity. This study has provided information about the regioselectivity of 1,3-dipolar cycloaddition reactions: regioselectivity may be controlled by π–π stacking state; the order of stability of stacking of the Ar and EWG part with the indane-1,3-dione part is: benzoyl group > phenyl group > nitro group.

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Acknowledgment

This work was financially supported by the grants from National Science Foundation of China (no. 50874092) and Scientific Research Program Funded by Shaanxi Provincial Education Department (program no. 08JK413, 11JK0560).

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Authors and Affiliations

  1. College of Chemistry and Chemical Engineering, Xi’an Shiyou University, Xi’an, 710065, People’s Republic of China

    Gang Chen, Jie Zhang & Ya Wu

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  1. Gang Chen
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  2. Jie Zhang
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  3. Ya Wu
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Correspondence to Gang Chen.

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Chen, G., Zhang, J. & Wu, Y. Synthesis and regiochemistry of spiro indane-1,3-dione compounds. Res Chem Intermed 38, 413–420 (2012). https://doi.org/10.1007/s11164-011-0357-0

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  • DOI: https://doi.org/10.1007/s11164-011-0357-0

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