Angewandte Chemie - International Edition
Angewandte Chemie - International Edition
5 years ago

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

Kinetic Resolution of 2-Substituted Indolines by N-Sulfonylation using an Atropisomeric 4-DMAP-N-oxide Organocatalyst
Nils J. Flodén, Daniel L. Dunklemann, Adriano Bauer, Alan C. Spivey, Jeffery Richardson, James I. Murray, Nico D. Fessner, Opetoritse Bob-Egbe, Henry S. Rzepa, Thomas Bürgi
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. A practical (re)solution: The kinetic resolution of 2-substituted indolines by catalytic N-sulfonylation is reported using an atropisomeric 4-dimethylaminopyridine-N-oxide organocatalyst (see scheme). Vibrational cicrcular dichroism is used to assign the absolute configuration of the catalyst and a qualitative model that accounts for the stereodiscrimination is proposed.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201700977

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