103796-39-0Relevant articles and documents
Kinetic Resolution of 2-Substituted Indolines by N-Sulfonylation using an Atropisomeric 4-DMAP-N-oxide Organocatalyst
Murray, James I.,Flodén, Nils J.,Bauer, Adriano,Fessner, Nico D.,Dunklemann, Daniel L.,Bob-Egbe, Opetoritse,Rzepa, Henry S.,Bürgi, Thomas,Richardson, Jeffery,Spivey, Alan C.
, p. 5760 - 5764 (2017/05/12)
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.