Recent Developments in the Application of Organometallic Chemistry to Amino Acid Synthesis

摘要

Alkylzinc iodide reagents derived from amino acids are useful intermediates for the synthesis of non-proteinogenic amino acids using metal-catalyzed coupling reactions. Dipolar aprotic solvents, specifically dimethylformamide, reduce the rate of elimination of β-amino alkylzinc reagents. These β-elimination reactions can be further suppressed by using trifluoroacetyl protection on nitrogen, which reduces intramolecular coordination to zinc, a key requirement in the elimination process. Acidic protons, specifically phenols, are tolerated in Negishi cross coupling reactions of these reagents.