| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1345598 | Tetrahedron: Asymmetry | 2016 | 4 Pages |
O- and N-trityl derivatives Ph3C∗-X-R∗ of chiral alcohols (X = O) and amines (X = NH) are known to produce strong and stereochemically predictable Cotton effects in the Electronic Circular Dichroism (ECD) spectra due to the preferred M or P helical conformation of the trityl group. With the use of ECD spectra in solution and crystal X-ray diffraction analysis, we demonstrate that in a chiral p-substituted trityl derivative p-R∗N(Me)-C6H4-C∗Ph2H, the stereochemical information is transmitted from a permanent stereogenic center R∗ to the dynamic C∗ stereogenic center of the trityl sensor via the para carbon atom, and not through the central carbon atom.
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(R)-4-Benzhydryl-N-methyl-N-(α-phenylethyl)-anilineC28H27N[α]D23 = +180 (c 0.15, CH2Cl2)Absolute configuration: (R)
