The first catalytic enantioselective Diels–Alder reactions of 1,2-dihydropyridine: efficient syntheses of optically active 2-azabicyclo[2.2.2]octanes with chiral BINAM derived Cr(III) salen complexes

We have synthesized a new family of enantiomerically enriched BINAM-derived Schiff base Cr(III) complexes and evaluated them as catalysts for Diels–Alder reactions. These complexes effectively catalyze, for the first time, the enantioselective Diels–Alder reactions between 1,2-dihydropyridine and N-acryloyloxazolidinone to afford 2-azabicyclo[2.2.2]octanes in high yields (89–99%) and with moderate to good enantioselectivities (79–85%).