Chemistry Letters, Vol.31, No.9, 900-901, 2002
Asymmetric Diels-Alder reactions catalyzed by chiral Ni(II)-binaphthyldiimine complexes
Ni(II)-N, N'-Bis(2-quinolylmethylene)-1,1'-binaphthyl-2,2'-diamine complex was found to be an efficient chiral Lewis acid catalyst for asymmetric Diels-Alder reactions (endo: up to 94% ee) between cyclopentadiene (1) and 3-alkenoyl-2-oxazolidinones (2). In the presence of Ni(11) catalyst (1 mol%), the reaction between cyclopentadiene and 3-acryloyl-2-oxazolidinone proceeded smoothly (85% yield) at -40degreesC with high enantioselectivity (endo: 90% ee).