Dual-Catalytic Asymmetric Reactions

Significance

Seidel and co-workers report a dual-catalysis approach to the asymmetric Steg­lich rearrangement (A) and a catalytic asymmetric addition of O-acylated azlactones to isoquinolines (B). O-Acylated azlactones were efficiently rearranged to the corresponding C-acylated products by combining a chiral hydrogen-bonding (HB) catalyst 1 with the achiral nucleophilic catalyst DMAP. The authors also demonstrated an unprecedented reaction of O-acylated azlactones using stoichiometric amounts of isoquinolines in the absence of a nucleophilic co-catalyst.