Department of Chemistry, Imperial College London, South Kensington Campus, London, SW7 2AZ, UK.
Université de Genève, Département de Chimie Physique, Quai Ernest-Ansermet 30, 1211, Genève 4, Switzerland.
Angew Chem Int Ed Engl. 2017 May 15;56(21):5760-5764. doi: 10.1002/anie.201700977. Epub 2017 Apr 26.
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.
首次描述了通过 N-磺酰化作用实现的催化动力学拆分。使用手性 4-二甲氨基吡啶-N-氧化物（4-DMAP-N-氧化物）有机催化剂拆分了 2-取代吲哚啉（s=2.6-19）。使用 2-异丙基-4-硝基苯基磺酰氯对于立体选择性至关重要，并能够通过硫代乙醇酸轻松脱保护磺酰胺产物。提出了一个定性模型来解释立体选择性。
