Chiral Phosphoric Acid-Catalyzed Enantioselective Construction of 2,3-Disubstituted Indolines

Highly enantio- and regioselective (3 + 2) formal cycloaddition of beta-substituted ene- and thioenecarbamates as well as cyclic enamides with quinone diimides catalyzed by a BINOL- and SPINOL-derived phosphoric acid is reported. A wide variety of 2,3-disubstituted 2-aminoindolines, including polycyclic ones, were prepared in generally high yields (up to 98%) with moderate to complete diastereoselectivities and in most cases excellent enantioselectivities (up to 99% ee).

Automated summary

A highly enantio- and regioselective (3 + 2) formal cycloaddition catalyzed by a BINOL- and SPINOL-derived phosphoric acid is reported, leading to the synthesis of a wide variety of 2,3-disubstituted 2-aminoindolines with generally high yields and excellent enantioselectivities. The reaction showed moderate to complete diastereoselectivities in most cases, producing products with up to 98% yield and up to 99% ee.