Synthesis and structure of 4-R,5-R-[5-(hydroxy-diphenyl-methyl)-2, 2-dimethyl-[1,3]dioxolan-4-yl]-phenyl-methanone, a chiral ligand building block |
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Authors: | Lawrence C. Thompson Kyle S. Knight William T. Pennington |
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Affiliation: | (1) Department of Chemistry, The University of Tennessee—Chattanooga, Chattanooga, Tennessee, 37403;(2) Department of Chemistry, Clemson University, Clemson, South Carolina |
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Abstract: | A triphenyl analog of taddol, 4-R,5-R-[5-(hydroxy-diphenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-phenyl-methanone, has been synthesized and structurally characterized. This molecule could act as a chiral ligand building block in the creation of tuned taddol analogs. Structural analysis of the title compound reveals that the hydroxyl group is involved in an intramolecular hydrogen bond and does not take part in any intermolecular interaction. Crystal packing is influenced by C–H O hydrogen bonding and phenyl phenyl interactions. Crystal data: Triclinic, P1 (No. 1), a = 5.9343(4) Å, b = 8.2367(17) Å, c = 10.987(2) Å, = 88.290(6), = 75.442(4), = 80.655(6), V = 512.86(15) Å3, Z = 1, Dcalc = 1.258 mg/m3. Final residual values were R1 = 0.0407 for 3022 observed data (I > 2s(I) ) and wR2 = 0.0941 for all 3524 unique data. |
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Keywords: | Taddol chiral ligand precursor triphenyl |
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