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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
A(1,3)-strain mediated epimerization of 2e,3e,5e,6e-tetraarylpiperidin-4-one oximes
M Srinivasan1, S Perumal, S Selvaraj
1Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, India.
Abstract:
A series of tri- and tetraarylpiperidin-4-one oximes were synthesized from 2e,3e,6e-tri- and 2e,3e,5e,6e-tetraarylpiperidin-4-ones, respectively. In the case of the latter compounds, oximation is accompanied by epimerization at C-5 to avoid the A(1,3)-strain between the oxime OH group and the 5e-aryl ring of the initially formed oxime resulting in 2e,3e,5a,6e-tetraarylpiperidin-4-one oximes. 1H, 13C and 2D NMR spectroscopic data were employed to characterize and investigate the stereochemistry of these compounds.
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