Catalytic Atropenantioselective Heteroannulation between Isocyanoacetates and Alkynyl Ketones: Synthesis of Enantioenriched Axially Chiral 3-Arylpyrroles

Abstract

We report herein the first examples of catalytic enantioselective synthesis of axially chiral 3-arylpyrroles. Reaction of α-isocyanoacetates with β-aryl-α,β-alkynic ketones in the presence of silver oxide and a phosphine ligand derived from Cinchona alkaloid occurred chemoselectively to afford enantioenriched 3-arylpyrroles in high yields with excellent enantiomeric excesses. The pyrrole ring was constructed de novo in this process.

Keywords: arylpyrrole; asymmetric synthesis; axial chirality; homogeneous catalysis; isocyanide.