1449677-23-9Relevant academic research and scientific papers
Enantioselective organocatalytic michael addition of cyclobutanones to nitroalkenes
Mailhol, Damien,Duque, Maria Del Mar Sanchez,Raimondi, Wilfried,Bonne, Damien,Constantieux, Thierry,Coquerel, Yoann,Rodriguez, Jean
, p. 3523 - 3532 (2013/02/25)
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 Bronsted 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.
