Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 21, Pages 5760-5764Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201700977
Keywords
asymmetric catalysis; indoline; kinetic resolution; organocatalysis; sulfonylation
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Funding
- EPSRC
- Institute of Chemical Biology (ICB, Imperial College London)
- SCI (Messel Scholarship)
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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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