%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