Never Underestimate The Influence Of 1,5-Diphenylpenta-1,4-dien-3-one

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Reactions of C-aryl-N-phenyl-nitrones with dibenzylideneacetone yielded pairs of diastereomeric bis-isoxazolidines in good to moderate yields. Both types of cycloadducts possessed identical regio- and stereo-selectivity. Molecular modeling studies revealed small difference in energy between the two isomers. Less stable isomer was converted to more stable one via partial cycloreversion followed by re-cycloaddition pathway. Zinc mediated acid catalyzed cycloreversion was observed for more stable diastereomer whereas less stable one yielded corresponding bis-1,3-aminoalcohols in similar condition. Some cycloadducts were screened for anticancer and antibacterial activity.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate