An efficient synthesis of gamma-amino acids and attempts to drive its enantioselectivity.
Addition of carboxylic acid dianions to bromoacetonitrile lead, in good yields,to the corresponding gamma-cyanoacids, which on hydrogenation yielded gamma-amino acids. This two step methodology improves upon previously described results. Poor e.e's resultedfrom our attempts to drive the enantioselectivity of this transformation by chiral amide induction.
Gil
Salvador
S
Department de Organic Chemistry, Universitat de València, Dr. Moliner 50, 46100 Burjassot, Spain.
Parra
Margarita
M
Rodríguez
Pablo
P
D000097:Acetonitriles / Q000737:chemistry; D000577:Amides / Q000737:chemistry; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry; D010648:Phenylacetates / Q000737:chemistry; D013237:Stereoisomerism
D000097:Acetonitriles; D000577:Amides; D000596:Amino Acids; D002264:Carboxylic Acids; D010648:Phenylacetates; C025136:phenylacetic acid; C032159:acetonitrile