%0 Generic %A Noole, Artur %A Järving, Ivar %A Werner, Franz %A Lopp, Margus %A Malkov, Andrei %A Kanger, Tõnis %D 2016 %T Organocatalytic Asymmetric Synthesis of 3‑Chlorooxindoles Bearing Adjacent Quaternary–Tertiary Centers %U https://acs.figshare.com/articles/dataset/Organocatalytic_Asymmetric_Synthesis_of_3_Chlorooxindoles_Bearing_Adjacent_Quaternary_Tertiary_Centers/2484961 %R 10.1021/ol302245b.s002 %2 https://ndownloader.figshare.com/files/4127734 %K chloroxoindole %K enantiomeric purities %K Adjacent %K enantiomerically %K Michael addition %K CentersA %K diastereoselectivitie %K Organocatalytic Asymmetric Synthesis %K synthesis %K chiral squaramide 10. Products %K quaternary %K center %K yield %K Quaternary %K chloroxindole %K stereoselective organocatalytic reaction %K nucleophile %K Chlorooxindole %K Bearing %K disubstituted %K methodology %K nitroolefin %K chlorooxindole %X 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. %I ACS Publications