Optical resolution of 1,16-dihydroxytetraphenylene by chiral gold(iii) complexation and its applications as chiral ligands in asymmetric catalysis |
| |
| Authors: | Jia Guo Wen-Bin Xiong Hao-Ran Ma Luoyi Fan You-Yun Zhou Henry N C Wong Jian-Fang Cui |
| |
| Institution: | Department of Chemistry, Southern University of Science and Technology, 1088 Xueyuan Blvd, Shenzhen 518055 China.; School of Science and Engineering, The Chinese University of Hong Kong (Shenzhen), 2001 Longxiang Blvd, Shenzhen 518172 China ; Department of Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong SAR China |
| |
| Abstract: | We report herein a novel approach involving optical resolution of (±)-1,16-dihydroxytetraphenylene (DHTP) by chiral gold(iii) complexation. This method features several key advantages, i.e., recyclability of chiral resolution reagents, feasibility of scaling up to gram quantities, and operational simplicity. On the basis of this method, which led to optically pure DHTP, a library of 2,15-diaryl (S)-DHTPs and several (S)-DHTP-derived phosphoramidite ligands were synthesized. Finally, the superior performance of a (S)-DHTP phosphoramidite ligand was demonstrated by efficient iridium-catalyzed asymmetric allylic alkynylation reactions.Chiral gold(iii) complex was found to be a “golden key” to unlock (±)-1,16-dihydroxytetraphenylene (DHTP), leading to enantiopure DHTP in a large quantity. This approach provided convenient access to 2,15-diaryl (S)-DHTPs and phosphoramidites. |
| |
| Keywords: | |
|
|
