Organobase catalysed one-pot exo-selective synthesis of meso-spiro[cyclohexanone-pyrandione] derivatives
authors Talhi, O; Abdeldjebar, H; Belmiloud, Y; Hassaine, R; Taibi, N; Valega, M; Paz, FAA; Brahimi, M; Bachari, K; Silva, AMS
nationality International
journal NEW JOURNAL OF CHEMISTRY
keywords CYCLOADDITION
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-1,5,9triones 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.
publisher ROYAL SOC CHEMISTRY
issn 1144-0546
isbn 1369-9261
year published 2017
volume 41
issue 19
beginning page 10790
ending page 10798
digital object identifier (doi) 10.1039/c7nj02168b
web of science category Chemistry, Multidisciplinary
subject category Chemistry
unique article identifier WOS:000411768600034
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