The groups first paper on asymmetric N-sulfonylation of indolines catalysed by an N-oxide catalyst is published in Angewandte Chemie.
James I. Murray, Nils J. Flodén, Adriano Bauer, Nico D. Fessner, Daniel L. Dunklemann, Opetoritse Bob-Egbe, Henry S. Rzepa, Thomas Bürgi, Jeffery Richardson and Alan C. Spivey, ‘Kinetic Resolution of 2-Substituted Indolines by N-Sulfonylation using an Atropisomeric 4-DMAP-N-oxide Organocatalyst’, Angew. Chem. Int. Ed. 2017, 56, 5760-5764. DOI: 10.1002/anie.201700977.
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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Professor Alan C Spivey
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