Aldehyde- and Ketone-Induced Tandem Decarboxylation-Coupling (Csp3−Csp) of Natural α-Amino Acids and Alkynes

2010/01/07 by Hai‐Peng Bi, Qingfeng Teng, Min Guan +4 · 4 citations
Chemistry · Chemical Engineering · #Catalytic C–H Functionalization Methods #Catalytic Cross-Coupling Reactions #Carbon dioxide utilization in catalysis

paper · doi:10.1021/jo902319h

openalex publication_date 2010/01/07 · openalex created_date 2016/06/24 · openalex updated_date 2026/06/28

Abstract

An interesting aldehyde- and ketone-induced intermolecular tandem decarboxylation-coupling (Csp(3)-Csp) catalyzed by copper with use of natural alpha-amino acids as starting materials is developed under neutral conditions with the production of CO(2) and H(2)O as the only byproducts. Various functionalized nitrogen-containing compounds were obtained by this method. In these processes, interesting regioselectivites of the alkylation were observed, which has been rationalized by the relative stability of proposed resonance structures based on computation methods.

Citations

• Palladium-Catalyzed Asymmetric Allylic α-Alkylation of Acyclic Ketones

Cited by

• Redox‐Neutral Copper(II) Carboxylate Catalyzed α‐Alkynylation of Amines
• The redox-A 3 reaction
• Nontraditional Reactions of Azomethine Ylides: Decarboxylative Three-Component Couplings of α-Amino Acids
• A3 coupling reaction [wikipedia]

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• Base-Catalyzed, Three-Component Coupling of Aldehydes, Terminal Aryl Acetylenes, and Amines: Application to Synthesis of Propargylamines
• A walk around the A3-coupling
• Oxidative copper-catalyzed synthesis of β-amino ketones from allyl alcohols and anilines