Efficient synthesis of beta2-amino acid by homologation of alpha-amino acids involving the Reformatsky reaction and Mannich-type imminium electrophile.
Development of new methods for the synthesis of beta-amino acids is important as polymers of these compounds are promising peptidomimetic candidates in medicinal chemistry. We report here our findings on a new and highly efficient general strategy for the synthesis of beta2-amino acids by homologation of alpha-amino acids, involving the Reformatsky reaction and Mannich-type imminium electrophile.
Moumne
Roba
R
Synthèses, Structures et Fonctions des Molécules Bioactives, CNRS/UMR 7613, Université Pierre et Marie Curie, 4, Place Jussieu, 75252, Paris Cedex 05, France.
Lavielle
Solange
S
Karoyan
Philippe
P
D000586:Amination; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D001966:Bromine / Q000737:chemistry; D004583:Electrons; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry; D005463:Fluoroacetates / Q000737:chemistry; D008352:Mannich Bases / Q000737:chemistry; D008745:Methylation; D015394:Molecular Structure; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D000596:Amino Acids; D004952:Esters; D005463:Fluoroacetates; D008352:Mannich Bases; D000644:Quaternary Ammonium Compounds; C014815:fluoroacetic acid; D001966:Bromine