Enantioselective Organocatalytic Michael Addition of Cyclobutanones to Nitroalkenes - Aix-Marseille Université Access content directly
Journal Articles Advanced Synthesis and Catalysis Year : 2012

Enantioselective Organocatalytic Michael Addition of Cyclobutanones to Nitroalkenes

Damien Mailhol
  • Function : Author
Wilfried Raimondi
  • Function : Author
Damien Bonne
Thierry Constantieux
  • Function : Author
Yoann Coquerel
Jean Rodriguez
  • Function : Correspondent author
  • PersonId : 921781

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Abstract

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 and versions

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

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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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