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 |
| 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: | 12 Mar 2012 11:35 |
| URI: | http://strathprints.strath.ac.uk/id/eprint/34203 |
Actions (login required)
| View Item |