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

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Coogan, Michael P. and Haigh, Robert and Hall, Adrian and Harris, Lisa D. and Hibbs, David E. and Jenkins, Robert L. and Jones, Claire L. and Tomkinson, Nicholas C. O. (2003) A new chiral diol derived from tetralone for the complexation of Lewis acids. Tetrahedron, 59 (37). pp. 7389-7395. ISSN 0040-4020 (https://doi.org/10.1016/S0040-4020(03)01127-X)

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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)]

ORCID iDs

Coogan, Michael P., Haigh, Robert, Hall, Adrian, Harris, Lisa D., Hibbs, David E., Jenkins, Robert L., Jones, Claire L. and Tomkinson, Nicholas C. O. ORCID logoORCID: https://orcid.org/0000-0002-5509-0133;
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