Kinetic Resolution of 2-Substituted Indolines by N -Sulfonylation using an Atropisomeric 4-DMAP- N -oxide Organocatalyst
- Murray, JI
- Flodén, NJ
- Bauer, A
- Fessner, ND
- Dunklemann, DL
- Bob-Egbe, O
- Rzepa, HS
- Bürgi, T
- Richardson, J
- Spivey, AC
Publication date
March 2017
DOI Publisher
Wiley Journal
Angewandte Chemie Language
EnglishAbstract
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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