Pd(II)/β-ICD-Cocatalyzed Asymmetric Route to Oxindole Scaffold via Cascade Reaction of Diazoacetamides and MBH-Carbonates.

Abstract

We report an efficient method for asymmetric synthesis of chiral oxindoles. Allyl palladium(II) chloride dimer (APC)-catalyzed, in combination with β-isocupreidine (β-ICD)-cocatalyzed, reaction of diazoacetamide with Morita-Baylis-Hillman (MBH) carbonates proves to be a facile protocol to access multifunctional oxindoles bearing a C-3 quaternary stereo center. This tandem reaction tolerates a wide variety of functional groups on the both aromatic rings. This method delivers a variety of chiral oxindoles in 50-75% yield and with up to 95:5 dr in most cases along with up to 93:7 er.