A new chiral diol derived from tetralone for the complexation of Lewis acids |
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Authors: | Michael P CooganRobert Haigh Adrian HallLisa D Harris David E HibbsRobert L Jenkins Claire L JonesNicholas C.O Tomkinson |
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Affiliation: | a Department of Chemistry, Cardiff University, PO Box 912, Cardiff, CF10 3TB, Wales, UK b Neurology Medicinal Chemistry III, GlaxoSmithKline R&D, The Frythe, Welwyn, Hertfordshire, AL6 9AR, UK |
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Abstract: | A new approach to the rational design of Lewis acids based on face-face π-π interactions is described. The synthesis of two novel diols (−)(1R,3R)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1,3-diol (−)-1 and (−)(1S,3R)-trans-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-3-diol (−)-9 is reported in six and five steps respectively starting from α-tetralone. Complexation of (−)(1R,3R)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1,3-diol (−)-1 to phenylboronic acid shows the interplanar distance between the boron atom and the aromatic ring to be 3.05 Å, which is ideal for the proposed interactions. |
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Keywords: | Lewis acids π-π interactions Jacobsen epoxidation |
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