Chiral Lewis acid promoted asymmetric Michael addition reaction of 2-(trimethylsilyloxy)furans

Article abstract of DOI:10.1055/s-1997-3235

Lewis acid promoted Michael addition of 2-(trimethylsilyloxy)furan to 3-[(E)-2-butenoyl]-1,3-oxazolidin-2-one (2) was examined. A 1:1 complex prepared from scandium triflate and 3,3′-bis(diethylaminomethyl)-1,1′-bi-2- naphthol 5b in situ showed excellent anti-selectivity and moderate enantioselectivity, while Cu(II)-bis(oxazolines) complex exhibited excellent enantioselectivity and moderate to good anti-selectivity.