Synthesis of Enantiopure C3-Symmetric Triangular Molecules
Corresponding Author
Dr. Tomoya Miura
Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto, 615-8510 Japan
Search for more papers by this authorTakayuki Nakamuro
Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto, 615-8510 Japan
Search for more papers by this authorDr. Scott G. Stewart
Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto, 615-8510 Japan
School of Chemistry and Biochemistry, The University of Western Australia, Australia
Search for more papers by this authorDr. Yuuya Nagata
Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto, 615-8510 Japan
Search for more papers by this authorCorresponding Author
Prof. Dr. Masahiro Murakami
Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto, 615-8510 Japan
Search for more papers by this authorCorresponding Author
Dr. Tomoya Miura
Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto, 615-8510 Japan
Search for more papers by this authorTakayuki Nakamuro
Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto, 615-8510 Japan
Search for more papers by this authorDr. Scott G. Stewart
Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto, 615-8510 Japan
School of Chemistry and Biochemistry, The University of Western Australia, Australia
Search for more papers by this authorDr. Yuuya Nagata
Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto, 615-8510 Japan
Search for more papers by this authorCorresponding Author
Prof. Dr. Masahiro Murakami
Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto, 615-8510 Japan
Search for more papers by this authorGraphical Abstract
My hat, it has three corners: Enantiopure C3-symmetric triangular macrocycles were synthesized by means of triple asymmetric cyclopropanation. This method is successfully extended to the synthesis of an enantiopure hydrocarbon, which owes its chirality to asymmetric distribution of H/D atoms on the benzene rings.
Abstract
An asymmetric synthesis of C3-symmetric triangular macrocycles is reported. 1-Methylsulfonyl-4-(4-vinylphenyl)-1,2,3-triazole undergoes a rhodium(II)-catalyzed cyclotrimerization to establish an enantiopure C3-symmetric triangular macrocycle motif. This method can be applied to the synthesis of an enantiopure hydrocarbon, which owes its chirality to asymmetric distribution of H/D atoms on the benzene rings.
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