Autocatalytic one pot orchestration for the synthesis of α-arylated, α-amino esters.
A novel acetyl chloride-mediated cascade transformation involving three components (benzyl carbamate, ethyl glyoxylate and arene nucleophiles) is reported. Aryl orthogonally protected α-amino acids are obtained in a one pot cascade, using a mild AcOH-AcCl system, via a critical autocatalytic dehydration-activation step ensuring an original and efficient Friedel-Crafts orchestration.
Department of Chemistry and Biochemistry, Florida Atlantic University, 777 Glades Road, Boca Raton, FL 33431, USA. sroche2@fau.edu.
Stéphane P
SP
Roche
Shyam S
SS
Samanta
Marine M J
MM
Gosselin
D000085:Acetates / Q000737:chemistry; D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry*; D001331:Automation; D002384:Catalysis; D002712:Chlorides / Q000737:chemistry; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000085:Acetates; D000596:Amino Acids; D002712:Chlorides; D004952:Esters; C081124:acetyl chloride