Enantioselective organocatalytic synthesis of α-allylated dihydroquinolines

Abstract

An enantioselective anion-binding catalyzed allylation method allowing for rapid access to chiral α-allyl dihydroquinolines has been developed. These chiral N-heterocycles were achieved in good yields (up to 90%) and with up to 89:11 e. r. using a tetrakis-triazole-based hydrogen-bond donor catalyst. The versatility of the allyl moiety in the formed products was further demonstrated by selective post-epoxidation and aziridination reactions, leading to highly decorated chiral molecules with up to four stereocenters and 94:6 e. r.