Practical enantioselective synthesis of axially chiral biaryl diphosphonates and dicarboxylates by cationic rhodium(I)/Segphos-catalyzed double [2 + 2 + 2] cycloaddition |
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| Authors: | Nishida Goushi Ogaki Shuichiro Yusa Yukinori Yokozawa Tohru Noguchi Keiichi Tanaka Ken |
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| Institution: | Department of Applied Chemistry, Graduate School of Engineering, and Instrumentation Analysis Center, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588, Japan. |
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| Abstract: | A cationic rhodium(I)/Segphos complex catalyzes a 2 + 2 + 2] cycloaddition of internal 1,6-diynes with a phosphonate- or ester-substituted 1,3-butadiyne leading to C(2)-symmetric axially chiral biaryl diphosphonates or dicarboxylates, respectively, in high yields with outstanding ee's. The use of a phosphonate- or ester-substituted 1,3-butadiyne as a cycloaddition partner and Segphos as a ligand is crucial for the success of this transformation. |
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