1398566-78-3Relevant academic research and scientific papers
Organocatalytic asymmetric synthesis of 3-chlorooxindoles bearing adjacent quaternary-tertiary centers
Noole, Artur,J?rving, Ivar,Werner, Franz,Lopp, Margus,Malkov, Andrei,Kanger, T?nis
, p. 4922 - 4925 (2012)
A new methodology was developed for the synthesis of enantiomerically enriched 3,3-disubstituted 3-chlorooxindoles 3 via a Michael addition of 3-chloroxindoles to nitroolefins 2, catalyzed by chiral squaramide 10. Products with adjacent quaternary-tertiar
Highly enantio-and diastereoselective generation of two quaternary centers in spirocyclopropanation of oxindole derivatives
Noole, Artur,Sucman, Natalia S.,Kabeshov, Mikhail A.,Kanger, T?nis,MacAev, Fliur Z.,Malkov, Andrei V.
, p. 14929 - 14933 (2012)
Spirocyclopropanes: Only one out of eight possible stereoisomers was obtained in the asymmetric cascade cyclopropanation of alkylidene oxindoles with ethyl 2-chloroacetoacetate. Improved catalyst design ensured that spirocyclopropyl oxindoles featuring tw
Organocatalytic asymmetric synthesis of 3-chlorooxindoles bearing adjacent quaternary-tertiary centers
Noole, Artur,Jaerving, Ivar,Werner, Franz,Lopp, Margus,Kanger, Tonis,Malkov, Andrei
supporting information, p. 4922 - 4925,4 (2012/12/12)
A new methodology was developed for the synthesis of enantiomerically enriched 3,3-disubstituted 3-chlorooxindoles 3 via a Michael addition of 3-chloroxindoles to nitroolefins 2, catalyzed by chiral squaramide 10. Products with adjacent quaternary-tertiary centers were isolated in excellent yields (up to 99%), high diastereoselectivities (up to 11:1), and enantiomeric purities (up to 92%). This is the first example where 3-chloroxoindoles 1 have been used as nucleophiles in a highly stereoselective organocatalytic reaction.
