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Article Dans Une Revue Advanced Synthesis and Catalysis Année : 2012

Enantioselective Organocatalytic Michael Addition of Cyclobutanones to Nitroalkenes

Damien Mailhol
  • Fonction : Auteur
Wilfried Raimondi
  • Fonction : Auteur
Damien Bonne
Thierry Constantieux
  • Fonction : Auteur
Yoann Coquerel
Jean Rodriguez
  • Fonction : Auteur correspondant
  • PersonId : 921781

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Résumé

Synthetic applications of cyclobutanones other than ring expansion and fragmentation reactions are rare. Herein, highly efficient diastereo- and enantioselective organocatalytic Michael additions of 2-substituted cyclobutanone derivatives to nitroalkenes are reported allowing the stereocontrolled creation of " all-carbon " quaternary centers. The approach relies on both the use of Brønsted base/hydrogen-bond donor bifunctional organocatalysts, and importantly, the specific stabilization and activation of cyclobutanone with a secondary amide moiety. The reaction was found to nicely accommodate a broad scope of substrates, allowing the control of up to three contiguous stereogenic centers. This work has opened new synthetic opportunities.

Dates et versions

hal-00801880 , version 1 (18-03-2013)

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Citer

Damien Mailhol, Maria del Mar Sanchez Duque, Wilfried Raimondi, Damien Bonne, Thierry Constantieux, et al.. Enantioselective Organocatalytic Michael Addition of Cyclobutanones to Nitroalkenes. Advanced Synthesis and Catalysis, 2012, 354, pp.3523-3532. ⟨10.1002/adsc.201200658⟩. ⟨hal-00801880⟩
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