Summary.
New γ-amino esters and amides were prepared by a radical 1,4-addition of carbon radicals to acrylic derivatives. α-Amino acids derivatives holding chiral auxiliaries as radical precursors and different chiral olefins were used and chiral induction on the C-γ center was discussed.
Similar content being viewed by others
References
DH Barton W Liu (1997) ArticleTitleThe invention of radical reactions. Part XXXVIII. Homologation of carboxylic acids with acrylamide and synthetic studies of 3-deoxy-D-arabino-2-heptulosonic acid (DAH) and its 4-epimer Tetrahedron 53 12037–12088
JR Burke RB Silverman (1991) ArticleTitleMechanism of inactivation of γ-aminobutyric acid aminotransferase by 4-amino-5-hexynoic acid (γ-ethynyl GABA) J Am Chem Soc 113 9329–9340 Occurrence Handle10.1021/ja00024a042 Occurrence Handle1:CAS:528:DyaK38XjsVehtg%3D%3D
SA Johannesen S Albu RG Hazell T Skrydstrup (2004) ArticleTitleRadical addition of nitrones to acrylates mediated by SmI2: asymmetric synthesis of γ-amino acids employing carbohydrate-based chiral auxiliaries Chem Commun 17 1962–1963 Occurrence Handle10.1039/b405141f
SM Nanavati RB Silverman (1991) ArticleTitleMechanisms of inactivation of γ-aminobutyric acid aminotransferase by the antiepilepsy drug γ-vinyl GABA (vigabatrin) J Am Chem Soc 113 9341–9349 Occurrence Handle10.1021/ja00024a043 Occurrence Handle1:CAS:528:DyaK38XjsVehsQ%3D%3D
D Riber T Skrydstrup (2003) ArticleTitleSmI2-Promoted radical addition of nitrones to α,β-unsaturated amides and esters: synthesis of α-amino acids via a nitrogen equivalent to the ketyl radical Org Lett 5 229–231 Occurrence Handle12529147 Occurrence Handle10.1021/ol027386y Occurrence Handle1:CAS:528:DC%2BD3sXmtw%3D%3D
A Trabocchi F Guarna A Guarna (2005) ArticleTitleγ- and δ-amino acids: synthetic strategies and relevant applications Curr Organ Chem 9 1129–1153
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Corvo, M., Pereira, M. Synthesis of γ-amino acid analogues from natural α-amino acids by a radical pathway. Amino Acids 32, 243–246 (2007). https://doi.org/10.1007/s00726-006-0378-y
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00726-006-0378-y