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

2018/11/27 by Sheng‐Cai Zheng, Qian Wang, Jieping Zhu · 1 citation
Chemistry · #Axial and Atropisomeric Chirality Synthesis #Molecular spectroscopy and chirality #Asymmetric Synthesis and Catalysis

paper · doi:10.1002/anie.201812654

openalex publication_date 2018/11/27 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/02

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.

Citations

• Silver‐Catalyzed Three‐Component 1,1‐Aminoacylation of Homopropargylamines: α‐Additions for Both Terminal Alkynes and Isocyanides

Cited by

• Zhu Jieping [wikipedia]

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