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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.
Affiliation
  • 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 in 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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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Borates / Diazonium Compounds / Aldehydes / Epoxy Compounds Language: En Journal: Angew Chem Int Ed Engl Year: 2019 Document type: Article
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Borates / Diazonium Compounds / Aldehydes / Epoxy Compounds Language: En Journal: Angew Chem Int Ed Engl Year: 2019 Document type: Article