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

2017/05/11 by Shuo Tong, Cyril Piemontesi, Qian Wang +2 · 2 citations
Chemistry · Biochemistry, Genetics and Molecular Biology · #Catalytic C–H Functionalization Methods #Catalytic Alkyne Reactions #Chemical Synthesis and Analysis

paper · doi:10.1002/anie.201704727

openalex publication_date 2017/05/11 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/02

Abstract

The reaction of secondary homopropargylamines, isocyanides, and water in the presence of a catalytic amount of silver acetate and subsequent purification by chromatography on silica gel afforded substituted proline amides in good to excellent yields. Primary homopropargylamines underwent a cyclizative Ugi-Joullié three-component reaction with isocyanides and carboxylic acids to afford functionalized N-acyl proline amides. High diastereoselectivity was observed in the synthesis of 4-alkoxy and 4,5-disubstituted proline derivatives. This work represents the first examples of a three-component cyclizative 1,1-aminoacylation of terminal alkynes.

Citations

• Cyclizations of Alkynes: Revisiting Baldwin’s Rules for Ring Closure

Cited by

• Catalytic Atropenantioselective Heteroannulation between Isocyanoacetates and Alkynyl Ketones: Synthesis of Enantioenriched Axially Chiral 3‐Arylpyrroles
• Zhu Jieping [wikipedia]

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