Synthesis ofN‐Acetyl‐α‐aminobutyric AcidviaAmidocarbonylation: A Case Study
- 19 March 2003
- journal article
- research article
- Published by Wiley in Advanced Synthesis & Catalysis
- Vol. 345 (4) , 510-516
- https://doi.org/10.1002/adsc.200390059
Abstract
The synthesis ofN‐acetyl‐α‐aminobutyric acid by amidocarbonylation of propionaldehyde with acetamide in the presence of palladium catalysts is studied in detail. The influence of various reaction conditions and compositions (e.g., the co‐catalysts acid and bromide) on the yield ofN‐acetyl‐α‐aminobutyric acid is shown. For the first time it is demonstrated that the palladium‐catalyzed amidocarbonylations of aldehydes can be run with significantly lower halide concentrations (<30 mol %) without a major yield decrease. While phosphine‐free catalyst systems give best yields at low CO pressure, phosphine‐ligated palladium catalysts lead to better yields at higher CO pressure. At low palladium loadings (<0.1 mol %), unwanted condensation reactions of propionaldehyde become increasingly competitive.Keywords
This publication has 41 references indexed in Scilit:
- Hydrothermal Synthesis and Structural Characterization of a Novel Organic‐Inorganic Hybrid Compound {[Cu (2, 2′‐bpy)2]2‐Mo8O26}Chinese Journal of Chemistry, 2002
- Palladium-catalyzed carbonylation of aryl halides — a detailed investigation of the alkoxycarbonylation of 4-bromoacetophenoneJournal of Molecular Catalysis A: Chemical, 2000
- Palladium-Catalyzed Synthesis of Substituted Hydantoins—A New Carbonylation Reaction for the Synthesis of Amino Acid DerivativesAngewandte Chemie International Edition in English, 1999
- Palladium-katalysierte Synthese von substituierten Hydantoinen – durch Carbonylierung zu AminosäurederivatenAngewandte Chemie, 1999
- First Amidocarbonylation with Nitriles for the Synthesis of N-Acyl Amino AcidsSynlett, 1999
- A new class of catalysts with superior activity and selectivity for amidocarbonylation reactionsJournal of Molecular Catalysis A: Chemical, 1998
- Chiral Magnesium Bis(sulfonamide) Complexes as Catalysts for the Merged Enolization and Enantioselective Amination of N-Acyloxazolidinones. A Catalytic Approach to the Synthesis of ArylglycinesJournal of the American Chemical Society, 1997
- Enantioselective Syntheses of α-, β-, and γ-Aryl Amino Acids and EstersThe Journal of Organic Chemistry, 1997
- The synthesis, properties, and applications ofN-acyl-α-aminoacidsRussian Chemical Reviews, 1995
- Synthesis of N-acyl amino-acids by a carbonylation reactionJournal of the Chemical Society D: Chemical Communications, 1971