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Enantioselective Organocatalytic Michael Addition of Cyclobutanones to Nitroalkenes

Damien Mailhol 1 Maria del Mar Sanchez Duque 1 Wilfried Raimondi 1 Damien Bonne 1 Thierry Constantieux 1 Yoann Coquerel 1 Jean Rodriguez 1, * 
* Corresponding author
1 STeRéO
ISM2 - Institut des Sciences Moléculaires de Marseille
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.
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Submitted on : Monday, March 18, 2013 - 4:07:18 PM
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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, Wiley-VCH Verlag, 2012, 354, pp.3523-3532. ⟨10.1002/adsc.201200658⟩. ⟨hal-00801880⟩



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