A new chiral diol derived from tetralone for the complexation of Lewis acids

Michael P. Coogan, Robert Haigh, Adrian Hall, Lisa D. Harris, David E. Hibbs, Robert L. Jenkins, Claire L. Jones, Nicholas C. O. Tomkinson

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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 (I) and (-)(1S,3R)-trans-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-3-diol (II) is reported in six and five steps resp. starting from α-tetralone. Complexation of (-)(1R,3R)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1,3-diol to phenylboronic acid shows the interplanar distance between the boron atom and the arom. ring to be 3.05 A, which is ideal for the proposed interactions. [on SciFinder(R)]
Original languageUndefined/Unknown
Pages (from-to)7389-7395
Number of pages7
JournalTetrahedron
Volume59
Issue number37
DOIs
Publication statusPublished - 2003

Keywords

  • tetralone
  • Lewis acids
  • chiral diol

Cite this

Coogan, M. P., Haigh, R., Hall, A., Harris, L. D., Hibbs, D. E., Jenkins, R. L., Jones, C. L., & Tomkinson, N. C. O. (2003). A new chiral diol derived from tetralone for the complexation of Lewis acids. Tetrahedron, 59(37), 7389-7395. https://doi.org/10.1016/S0040-4020(03)01127-X