Synthesis of Rigid and Optically Active Bis(binaphthyl) Cyclic Compounds

Abstract

Optically active cyclic bis(binaphthyl)s (4a–d), which are composed of aromatics, ethers, and ketonic carbonyls, were synthesized through a two‐step nucleophilic aromatic substitution reaction. Bis(binaphthyl) cyclic compounds (4a and 4b) were obtained in moderate yields when difluoride 3a and 3b were employed. On the other hand, bis(binaphthyl)s 4c and 4d were scarcely obtained when 3c and 3d were employed.

Keywords:

• bis(binaphthyl)
• optically active cycles
• two‐step nucleophilic aromatic substitution reaction

Acknowledgment

This work was supported by a Grant‐in‐Aid for Young Scientists (B) (No. 18750185) from the Ministry of Education, Culture, Sports, Science, and Technology of Japan. We are grateful to Hideaki Oike at Tokyo University of Agriculture and Technology for measurement of MALDI‐TOF MS.