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

De novo construction of pyrrole: In the presence of a catalytic amount of Ag₂O and chiral phosphine ligand, the heteroannulation between isocyanoacetates and alkynyl ketones afforded the axially chiral 3‐arylpyrroles in good yields with excellent enantioselectivities.

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.

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