CATALYTIC ASYMMETRIC AZA-DIELS-ALDER REACTIONS USING A CHIRAL LANTHANIDE LEWIS-ACID - ENANTIOSELECTIVE SYNTHESIS OF TETRAHYDROQUINOLINE DERIVATIVES USING A CATALYTIC AMOUNT OF A CHIRAL SOURCE

In the presence of a catalytic amount of the chiral ytterbium Lewis ac id, which was prepared from Yb(OTf)(3), (R)-(+)-BINOL, diazabicyclo[5. 4.0]undec-7-ene (DBU), and an additive, achiral imines reacted with ac hiral dienophiles to afford the corresponding tetrahydroquinoline deri vatives in high yields with high diastereo- and enantioselectivities. This is the first example of aza Diels-Alder reactions using a catalyt ic amount of a chiral source. Copyright (C) 1996 Elsevier Science Ltd