N-heterocyclic carbene-catalyzed stereoselective cascade reaction: synthesis of functionalized tetrahydroquinolines.

ABSTRACT

The first N-heterocyclic carbene-catalyzed stereoselective aza-Michael-Michael-lactonization cascade reaction of 2'-aminophenylenones and 2-bromoenals for the construction of chiral functionalized tetrahydroquinolines with three consecutive stereogenic centers has been achieved in high yields (up to 98%) with excellent diastereo- (>251) and enantioselectivities (up to 98.7% ee).