An Asymmetric Organocatalytic Quadruple Cascade Initiated by a Friedel-Crafts-Type Reaction with Electron-Rich Arenes

摘要

An organocatalytic quadruple domino reaction initiated by a Friedel-Crafts-type reaction of electron-rich arenes is described. The procedure involving up to three different Michael acceptors afforded highly functionalized cyclohexenecarbalde-hydes bearing an aniline moiety, which are of great pharmaceutical and agricultural interest. This di-phenylprolinol trimethylsilyl ether-catalyzed reaction also generates up to 4 contiguous stereocenters. It could be shown that various functional groups are tolerated and all products were obtained with very good diastereo- and excellent enantioselectivi- ty.