Catalyst-free racemic and H₂O/CPA-catalyzed asymmetric regio-reversed domino processes of triketone enones with azlactones

Abstract

Regio-reversed domino processes of triketone enones with azlactones have been established. As opposite to the previous β-addition-triggered domino processes, this protocol is initiated by regio-reversed α-addition. Under catalyst-free conditions, the...

Diastereodivergent and Regioselective Synthesis of Tetrahydrofuro[2,3-b]furans with Four Consecutive Stereocenters

“…Recently, the Lu group developed a phosphine-catalyzed domino transformation of triketone enones with γ-substituted allenoates to form bicyclic furofurans in good yields with excellent enantioselectivities (Scheme B). Very recently, our group disclosed CPA-catalyzed regio-reversed domino processes of triketone enones with azlactones, giving a variety of bicyclic furofurans bearing vicinal quaternary carbons with good enantioselectivities (Scheme C). Inspired by these advances and in continuation to our interest toward the construction of polyfunctional heterocycles, herein, we describe our study on base-catalyzed diastereodivergent domino processes of triketone enones with arylacetaldehydes for the synthesis of tetrahydrofuro­[2,3- b ]­furans with four consecutive stereocenters (Scheme D).…”