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Synthesis of macrocyclic 1,1′-biarenol derivatives by the tandem Claisen rearrangement and their binding properties |
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| Authors: | Hiroaki Yoshida Kazuhisa Hiratani |
| Institution: | a Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-8656, Japan b Department of Applied Chemistry, Utsunomiya University, Youtou, Utsunomiya, Tochigi 321-8585, Japan |
| Abstract: | Crown ether-type macrocycles consisting of an enantiopure biarenol derivative and an oligoethylene glycol were synthesized by the Lewis acid-mediated tandem Claisen rearrangement. This is the first example of the successful application of the tandem Claisen rearrangement to the synthesis of enantiopure macrocyclic biarenol derivatives. The enantiopure macrocyclic biarenols were found to form 1:1 complexes with amino acid salts and to discriminate their chirality. |
| Keywords: | Tandem Claisen rearrangement 1 1&prime -Bi-2-naphthol Chiral recognition Host-guest complex Amino acid salt |
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