Radical addition of nitrones to acrylates mediated by SmI2: asymmetric synthesis of gamma-amino acids employing carbohydrate-based chiral auxiliaries.
Alkyl nitrones possessing N-substituted sugars as chiral auxiliaries were found to effectively undergo an SmI(2)-mediated radical addition to n-butyl acrylate affording gamma-amino acid derivatives with high diastereomeric control.
Johannesen
Sine A
SA
Department of Chemistry, University of Aarhus, Langelandsgade 140, 8000 Aarhus C, Denmark.
Albu
Silvia
S
Hazell
Rita G
RG
Skrydstrup
Troels
T
D000179:Acrylates / Q000737:chemistry*; D000596:Amino Acids / Q000138:chemical synthesis*; D002241:Carbohydrates / Q000737:chemistry*; D005609:Free Radicals / Q000737:chemistry; D008956:Models, Chemical; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000737:chemistry*; D011506:Proteins / Q000737:chemistry* / Q000494:pharmacology; D013237:Stereoisomerism
D000179:Acrylates; D000596:Amino Acids; D002241:Carbohydrates; D005609:Free Radicals; D009589:Nitrogen Oxides; D011506:Proteins; C015388:nitrones; C080380:sperm motility inhibitor 2; C032490:n-butyl acrylate