@article{oai:nagoya.repo.nii.ac.jp:02001527, author = {Hatano, Manabu and Toh, Kohei and Ishihara, Kazuaki}, issue = {24}, journal = {Organic Letters}, month = {Dec}, note = {A hydrogen bonding network in chiral Brønsted acid catalysts is important for the construction of a chiral cavity and the enhancement of catalytic activity. In this regard, we developed a highly enantioselective aza-Friedel–Crafts reaction of indoles and pyrroles with acyclic α-ketimino esters in the presence of a chiral C1-symmetric BINOL-derived bis(phosphoric acid) catalyst. The desired alkylation products with chiral quaternary carbon centers were obtained in high yields with high enantioselectivities on up to a 1.2-g scale with 0.2 mol % catalyst loading. Interestingly, the absolute configurations of the products from indoles and pyrroles were opposite even with the use of the same chiral catalyst. Moreover, preliminary mechanistic considerations disclosed that a unique hydrogen bonding network with or without π–π interactions among the catalyst and substrates might partially play a pivotal role.}, pages = {9614--9620}, title = {Enantioselective Aza-Friedel–Crafts Reaction of Indoles and Pyrroles Catalyzed by Chiral C1-Symmetric Bis(phosphoric Acid)}, volume = {22}, year = {2020} }