Literature DB >> 28444918

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

James I Murray1, Nils J Flodén1, Adriano Bauer1, Nico D Fessner1, Daniel L Dunklemann1, Opetoritse Bob-Egbe1, Henry S Rzepa1, Thomas Bürgi2, Jeffery Richardson3, Alan C Spivey1.   

Abstract

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.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  asymmetric catalysis; indoline; kinetic resolution; organocatalysis; sulfonylation

Year:  2017        PMID： 28444918     DOI： 10.1002/anie.201700977

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  3 in total

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Authors:  Nicholas Carter; Xiabing Li; Lewis Reavey; Anthony J H M Meijer; Iain Coldham
Journal:  Chem Sci       Date:  2017-12-14       Impact factor: 9.825

2.  Selective dehydrogenation of small and large molecules by a chloroiridium catalyst.

Authors:  Kuan Wang; Lan Gan; Yuheng Wu; Min-Jie Zhou; Guixia Liu; Zheng Huang
Journal:  Sci Adv       Date:  2022-09-23       Impact factor: 14.957

3.  Enantioselective radical process for synthesis of chiral indolines by metalloradical alkylation of diverse C(sp3)-H bonds.

Authors:  Xin Wen; Yong Wang; X Peter Zhang
Journal:  Chem Sci       Date:  2018-05-14       Impact factor: 9.825
  3 in total

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