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Kinetic Resolution of 2-Substituted Indolines by N-Sulfonylation using an Atropisomeric 4-DMAP-N-oxide Organocatalyst.

James I Murray, Nils J Flodén, Adriano Bauer, Nico D Fessner, Daniel L Dunklemann, Opetoritse Bob-Egbe, Henry S Rzepa, Thomas Bürgi, Jeffery Richardson, Alan C Spivey
Angewandte Chemie 2017 April 27
The first catalytic kinetic resolution by N-sulfonylation is described. 2-Substituted indolines are resolved (s=2.6-19) using an atropisomeric 4-dimethylaminopyridine-N-oxide (4-DMAP-N-oxide) organocatalyst. Use of 2-isopropyl-4-nitrophenylsulfonyl chloride is critical to the stereodiscrimination and enables facile deprotection of the sulfonamide products with thioglycolic acid. A qualitative model that accounts for the stereodiscrimination is proposed.

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