Recently, Professor Shi Feng and her team’s latest research achievement was published in Angewandte Chemie, arousing much attention among international academic circle.
“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.”
“In summary, we have established the first catalytic asymmetric construction of 3,3′‐bisindole skeletons bearing both axial and central chirality, and it takes advantage of a CPA‐catalyzed reaction of 2‐substituted 3,3′‐bisindoles with 3‐indolylmethanols. This reaction also represents the first highly enantioselective construction of axially chiral 3,3′‐bisindole skeletons, a new member for the family of axially chiral biaryls. By introducing a bulky group to the ortho‐position of prochiral 3,3′‐bisindoles, a series of 3,3′‐bisindole derivatives with axial and central chirality were afforded in high yields and excellent stereoselectivities. This reaction not only meets the challenges in catalytic enantioselective construction of five‐membered axially chiral biaryls, but also provides a good example for simultaneously controlling axial and central chirality in one operation. In addition, this approach serves as a new strategy for catalytic enantioselective construction of axially chiral biaryl backbones from prochiral substrates.”
It is reported that the paper had been selected as “Frontispiece” and “hot paper”, and as special issue “Women in Chemistry” for celebrating International Women’s Day. This issue collected some influential female researchers’ representative work among the world. The first author and co-first author are JSNU postgraduate students Ma Chun and Jiang Fei respectively.