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Organobase catalysed one-pot exo-selective synthesis of meso-spiro[cyclohexanone-pyrandione] derivatives

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Abstract

An exo-selective one-pot synthesis of novel spiro[cyclohexanone-pyrandione] derivatives through two sequential organobase-catalysed 1,4-conjugate additions of pyran-2,4-dione precursors on diarylideneacetone derivatives is described. The resulting 7,11-diaryl-2-oxaspiro[5.5]undec-3-ene-1,5,9-triones were obtained as a 2 : 1 mixture of exo- and endo-diastereomers and adopt a meso-form due to the bilateral symmetry existing in the scaffold. Chiral-HPLC, NMR and single-crystal X-ray diffraction (including synchrotron data) have been used to elucidate the spiro[cyclohexanone-pyrandione] structure, showing therefore the exo/endo-diastereomers obtained in a meso-form, the cis-7,11-diaryl configuration (equatorial position) and different conformational changes in the cyclohexanone skeleton both in liquid and solid states. DFT studies proved the exo-stereoselectivity of the reaction by determining the exo/cis equatorial–equatorial configuration as the most thermodynamically stable form of our spiro[cyclohexanone-pyrandione] skeleton, while the structural substitution has no effect.

Graphical abstract: Organobase catalysed one-pot exo-selective synthesis of meso-spiro[cyclohexanone-pyrandione] derivatives

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Publication details

The article was received on 17 Jun 2017, accepted on 17 Aug 2017 and first published on 18 Aug 2017


Article type: Paper
DOI: 10.1039/C7NJ02168B
Citation: New J. Chem., 2017, Advance Article
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    Organobase catalysed one-pot exo-selective synthesis of meso-spiro[cyclohexanone-pyrandione] derivatives

    O. Talhi, H. Abdeldjebar, Y. Belmiloud, R. Hassaine, N. Taibi, M. Válega, F. A. A. Paz, M. Brahimi, K. Bachari and A. M. S. Silva, New J. Chem., 2017, Advance Article , DOI: 10.1039/C7NJ02168B

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