Nontraditional Reactions of Azomethine Ylides: Decarboxylative Three-Component Couplings of α-Amino Acids

2010/01/27 by Chen Zhang, Daniel Seidel · 4 citations
Chemistry · #1,3-Dipolar cycloaddition #Amino acid #Azomethine ylide #Biochemistry #Catalysis #Catalytic C–H Functionalization Methods #Chemistry #Click Chemistry and Applications #Component (thermodynamics) #Cycloaddition #Decarboxylation #Organic chemistry #Synthesis and Catalytic Reactions

paper · doi:10.1021/ja910719x

openalex publication_date 2010/01/27 · openalex created_date 2016/06/24 · openalex updated_date 2026/07/01

Abstract

New reactions of azomethine ylides with nontraditional dipolarophiles are reported. Azomethine ylides, formed in situ via decarboxylative condensations of alpha-amino acids with aldehydes, undergo reactions with naphthols, indoles, alkynes, and nitroalkanes.

Citations

• Aldehyde- and Ketone-Induced Tandem Decarboxylation-Coupling (Csp3−Csp) of Natural α-Amino Acids and Alkynes
• The Copper‐Catalyzed Decarboxylative Coupling of the sp3‐Hybridized Carbon Atoms of α‐Amino Acids

Cited by

• CuI-Catalyzed C1-Alkynylation of Tetrahydroisoquinolines (THIQs) by A3 Reaction with Tunable Iminium Ions
• Redox‐Neutral Copper(II) Carboxylate Catalyzed α‐Alkynylation of Amines
• The redox-A 3 reaction
• A3 coupling reaction [wikipedia]

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• The Huisgen Reaction: Milestones of the 1,3‐Dipolar Cycloaddition
• Aldehyde- and Ketone-Induced Tandem Decarboxylation-Coupling (Csp3−Csp) of Natural α-Amino Acids and Alkynes
• A walk around the A3-coupling
• The Thiazole Aldehyde Synthesis