Strathprints Home | Open Access | Browse | Search | User area | Copyright | Help | Library Home | SUPrimo

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

Full text not available in this repository. (Request a copy from the Strathclyde author)

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
Notes: M1 - Copyright (C) 2011 American Chemical Society (ACS). All Rights Reserved. CAPLUS AN 2003:690005(Journal)
Keywords: tetralone , Lewis acids , chiral diol, Chemistry, Biochemistry, Organic Chemistry, Drug Discovery
Subjects: Science > Chemistry
Department: Faculty of Science > Pure and Applied Chemistry
Related URLs:
    Depositing user: Pure Administrator
    Date Deposited: 20 Oct 2011 15:17
    Last modified: 05 Sep 2014 11:40
    URI: http://strathprints.strath.ac.uk/id/eprint/34203

    Actions (login required)

    View Item