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Asymmetric and Geometry-Selective α-Alkenylation of α-Amino Acids.
Abas, Hossay; Mas-Roselló, Josep; Amer, Mostafa Mahmoud; Durand, Derek J; Groleau, Robin R; Fey, Natalie; Clayden, Jonathan.
Afiliación
  • Abas H; School of Chemistry, Cantock's Close, Bristol, BS8 1TS, UK.
  • Mas-Roselló J; School of Chemistry, Cantock's Close, Bristol, BS8 1TS, UK.
  • Amer MM; School of Chemistry, Cantock's Close, Bristol, BS8 1TS, UK.
  • Durand DJ; School of Chemistry, Cantock's Close, Bristol, BS8 1TS, UK.
  • Groleau RR; School of Chemistry, Cantock's Close, Bristol, BS8 1TS, UK.
  • Fey N; School of Chemistry, Cantock's Close, Bristol, BS8 1TS, UK.
  • Clayden J; School of Chemistry, Cantock's Close, Bristol, BS8 1TS, UK.
Angew Chem Int Ed Engl ; 58(8): 2418-2422, 2019 02 18.
Article en En | MEDLINE | ID: mdl-30600901
Both E- and Z-N'-alkenyl urea derivatives of imidazolidinones may be formed selectively from enantiopure α-amino acids. Generation of their enolate derivatives in the presence of K+ and [18]crown-6 induces intramolecular migration of the alkenyl group from N' to Cα with retention of double bond geometry. DFT calculations indicate a partially concerted substitution mechanism. Hydrolysis of the enantiopure products under acid conditions reveals quaternary α-alkenyl amino acids with stereodivergent control of both absolute configuration and double bond geometry.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Angew Chem Int Ed Engl Año: 2019 Tipo del documento: Article Pais de publicación: Alemania
Texto completo
Añadir a Mi BVS
Imprimir
XML
PubMed Links
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Angew Chem Int Ed Engl Año: 2019 Tipo del documento: Article Pais de publicación: Alemania