Organocatalytic Asymmetric Synthesis of Tetrahydroquinolines from ortho -Aminophenyl para -Quinone Methides.

The asymmetric catalytic [4 + 2] cycloannulation of -aminophenyl -QMs with different types of alkenes for the construction of tetrahydroquinolines containing three contiguous stereogenic centers was developed. This is the first example of catalytic asymmetric cycloannulation of -aminophenyl -QMs. This reaction exhibits excellent functional group tolerance. Excellent yields, exclusive diastereoselectivities, and high enantioselectivities were obtained in this efficient organocatalytic reaction.