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 (https://doi.org/10.1016/S0040-4020(03)01127-X)
Full text not available in this repository.Request a copyAbstract
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 Dates: DateEvent2003PublishedSubjects: Science > Chemistry Department: Faculty of Science > Pure and Applied Chemistry Depositing user: Pure Administrator Date deposited: 20 Oct 2011 14:17 Last modified: 08 Apr 2024 19:29 URI: https://strathprints.strath.ac.uk/id/eprint/34203