Design and Catalytic Asymmetric Construction of Axially Chiral 3,3′-Bisindole Skeletons
Chun Ma
School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, 221116 P. R. China
These authors contributed equally to this work.
Search for more papers by this authorFei Jiang
School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, 221116 P. R. China
These authors contributed equally to this work.
Search for more papers by this authorFeng-Tao Sheng
School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, 221116 P. R. China
Search for more papers by this authorDr. Yinchun Jiao
School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan, 411201 P. R. China
Search for more papers by this authorDr. Guang-Jian Mei
School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, 221116 P. R. China
Search for more papers by this authorCorresponding Author
Prof. Dr. Feng Shi
School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, 221116 P. R. China
Search for more papers by this authorChun Ma
School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, 221116 P. R. China
These authors contributed equally to this work.
Search for more papers by this authorFei Jiang
School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, 221116 P. R. China
These authors contributed equally to this work.
Search for more papers by this authorFeng-Tao Sheng
School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, 221116 P. R. China
Search for more papers by this authorDr. Yinchun Jiao
School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan, 411201 P. R. China
Search for more papers by this authorDr. Guang-Jian Mei
School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, 221116 P. R. China
Search for more papers by this authorCorresponding Author
Prof. Dr. Feng Shi
School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, 221116 P. R. China
Search for more papers by this authorGraphical Abstract
Bulk up: The first catalytic asymmetric construction of 3,3′-bisindole skeletons bearing axial and central chirality has been established by organocatalytic asymmetric addition reactions of 2-substituted 3,3′-bisindoles with electrophiles. This reaction also represents the first highly enantioselective construction of axially chiral 3,3′-bisindole skeletons, and utilizes the strategy of introducing a bulky group to the ortho-position of prochiral 3,3′-bisindoles.
Abstract
The first catalytic asymmetric construction of 3,3′-bisindole skeletons bearing both axial and central chirality has been established by organocatalytic asymmetric addition reactions of 2-substituted 3,3′-bisindoles with 3-indolylmethanols (up to 98 % yield, all >95:5 d.r., >99 % ee). This reaction also represents the first highly enantioselective construction of axially chiral 3,3′-bisindole skeletons, and utilizes the strategy of introducing a bulky group to the ortho-position of prochiral 3,3′-bisindoles. This reaction not only provides a good example for simultaneously controlling axial and central chirality in one operation, but also serves as a new strategy for catalytic enantioselective construction of axially chiral 3,3′-bisindole backbones from prochiral substrates.
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