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Catalytic Asymmetric Epoxidation of Aldehydes with Two VANOL-Derived Chiral Borate Catalysts.
Gupta, Anil K; Yin, Xiaopeng; Mukherjee, Munmun; Desai, Aman A; Mohammadlou, Aliakbar; Jurewicz, Kelsee; Wulff, William D.
Afiliación
  • Gupta AK; Department of Chemistry, Michigan State University, East Lansing, MI, 48824, USA.
  • Yin X; Department of Chemistry, Michigan State University, East Lansing, MI, 48824, USA.
  • Mukherjee M; Department of Chemistry, Michigan State University, East Lansing, MI, 48824, USA.
  • Desai AA; Department of Chemistry, Michigan State University, East Lansing, MI, 48824, USA.
  • Mohammadlou A; Department of Chemistry, Michigan State University, East Lansing, MI, 48824, USA.
  • Jurewicz K; Department of Chemistry, Michigan State University, East Lansing, MI, 48824, USA.
  • Wulff WD; Department of Chemistry, Michigan State University, East Lansing, MI, 48824, USA.
Angew Chem Int Ed Engl ; 58(11): 3361-3367, 2019 03 11.
Article en En | MEDLINE | ID: mdl-30556933
ABSTRACT
A highly diastereo- and enantioselective method for the epoxidation of aldehydes with α-diazoacetamides has been developed with two different borate ester catalysts of VANOL. Both catalytic systems are general for aromatic, aliphatic, and acetylenic aldehydes, giving high yields and inductions for nearly all cases. One borate ester catalyst has two molecules of VANOL and the other only one VANOL. Catalysts generated from BINOL and VAPOL are ineffective catalysts. An application is shown for access to the side-chain of taxol.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Boratos / Compuestos de Diazonio / Aldehídos / Compuestos Epoxi Idioma: En Revista: Angew Chem Int Ed Engl Año: 2019 Tipo del documento: Article País de afiliación: Estados Unidos
Texto completo
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XML
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Boratos / Compuestos de Diazonio / Aldehídos / Compuestos Epoxi Idioma: En Revista: Angew Chem Int Ed Engl Año: 2019 Tipo del documento: Article País de afiliación: Estados Unidos