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

Diana Becerra (1) , Wilfried Raimondi (1) , Daniel Dauzonne (2) , Thierry Constantieux (1) , Damien Bonne (1) , Jean Rodriguez (1)

1 ISM2 - Institut des Sciences Moléculaires de Marseille
2 CBMCT - UMR 3666 / U1143 - Chimie biologique des membranes et ciblage thérapeutique

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%.

Mots clés: dihydrofurans; organocatalysis; domino Michael/alkylation; Takemoto catalyst; (Z)--chloro--nitrostyrenes

Domaines: Chimie organique

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. Synthesis: Journal of Synthetic Organic Chemistry, 2016, 49 (01), pp.195-201. ⟨10.1055/s-0035-1562446⟩. ⟨hal-01533770⟩