Enantioselective Organocatalyzed Consecutive Synthesis of Alkyl 4,5-Dihydrofuran-2-carboxylates from α-Keto Esters and (Z)-β-Chloro-β-nitrostyrenes - MédiHAL Accéder directement au contenu
Image (Illustration) Année : 2016

Enantioselective Organocatalyzed Consecutive Synthesis of Alkyl 4,5-Dihydrofuran-2-carboxylates from α-Keto Esters and (Z)-β-Chloro-β-nitrostyrenes

Résumé

Alkyl 4,5-dihydrofuran-2-carboxylates can be efficiently ob- tained via an enantioselective organocatalyzed consecutive reaction between _-keto esters and (Z)-(2-chloro-2-nitroethenyl)benzenes. The overall sequence combines a (R,R)-TUC-catalyzed Michael addition with a DABCO-promoted intramolecular O-alkylation leading to the title products as single diastereomers with enantiomeric excesses from 86% up to 97%.

Dates et versions

medihal-01723185 , version 1 (05-03-2018)

Licence

Domaine public

Identifiants

  • HAL Id : medihal-01723185 , version 1

Citer

Diana Becerra, Wilfried Raimondi, Daniel Dauzonne, Thierry Constantieux, Damien Bonne, et al.. Enantioselective Organocatalyzed Consecutive Synthesis of Alkyl 4,5-Dihydrofuran-2-carboxylates from α-Keto Esters and (Z)-β-Chloro-β-nitrostyrenes. Illustration. France. 2016. ⟨medihal-01723185⟩
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