TY - DATA T1 - Organocatalytic Asymmetric Synthesis of 3‑Chlorooxindoles Bearing Adjacent Quaternary–Tertiary Centers PY - 2016/02/20 AU - Artur Noole AU - Ivar Järving AU - Franz Werner AU - Margus Lopp AU - Andrei Malkov AU - Tõnis Kanger UR - https://acs.figshare.com/articles/dataset/Organocatalytic_Asymmetric_Synthesis_of_3_Chlorooxindoles_Bearing_Adjacent_Quaternary_Tertiary_Centers/2484961 DO - 10.1021/ol302245b.s002 L4 - https://ndownloader.figshare.com/files/4127734 KW - chloroxoindole KW - enantiomeric purities KW - Adjacent KW - enantiomerically KW - Michael addition KW - CentersA KW - diastereoselectivitie KW - Organocatalytic Asymmetric Synthesis KW - synthesis KW - chiral squaramide 10. Products KW - quaternary KW - center KW - yield KW - Quaternary KW - chloroxindole KW - stereoselective organocatalytic reaction KW - nucleophile KW - Chlorooxindole KW - Bearing KW - disubstituted KW - methodology KW - nitroolefin KW - chlorooxindole N2 - 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. ER -