Kinetic Resolution of 2-Substituted Indolines by N-Sulfonylation using an Atropisomeric 4-DMAP-N-oxide Organocatalyst.
- Murray JI Department of Chemistry, Imperial College London, South Kensington Campus, London, SW7 2AZ, UK.
- Flodén NJ Department of Chemistry, Imperial College London, South Kensington Campus, London, SW7 2AZ, UK.
- Bauer A Department of Chemistry, Imperial College London, South Kensington Campus, London, SW7 2AZ, UK.
- Fessner ND Department of Chemistry, Imperial College London, South Kensington Campus, London, SW7 2AZ, UK.
- Dunklemann DL Department of Chemistry, Imperial College London, South Kensington Campus, London, SW7 2AZ, UK.
- Bob-Egbe O Department of Chemistry, Imperial College London, South Kensington Campus, London, SW7 2AZ, UK.
- Rzepa HS Department of Chemistry, Imperial College London, South Kensington Campus, London, SW7 2AZ, UK.
- Bürgi T Université de Genève, Département de Chimie Physique, Quai Ernest-Ansermet 30, 1211, Genève 4, Switzerland.
- Richardson J Eli Lilly and Company Limited, Erl Wood Manor, Windlesham, Surrey, GU20 6PH, UK.
- Spivey AC Department of Chemistry, Imperial College London, South Kensington Campus, London, SW7 2AZ, UK.
- 2017-04-27
Published in:
- Angewandte Chemie (International ed. in English). - 2017
English
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.
- Language
-
- English
- Open access status
- green
- Identifiers
-
- DOI 10.1002/anie.201700977
- PMID 28444918
- Persistent URL
- https://sonar.ch/global/documents/269233
Statistics
Document views: 32
File downloads:
- Full-text: 0