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

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

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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)]

Item type: Article
ID code: 34203
Keywords: tetralone , Lewis acids , chiral diol, Chemistry, Biochemistry, Organic Chemistry, Drug Discovery
Subjects: Science > Chemistry
Department: Faculty of Science > Pure and Applied Chemistry
Depositing user: Pure Administrator
Date Deposited: 20 Oct 2011 14:17
Last modified: 21 May 2015 13:48
URI: http://strathprints.strath.ac.uk/id/eprint/34203

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