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Title

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

Authors
Murray, James I.
Flodén, Nils J.
Bauer, Adriano
Fessner, Nico D.
Dunklemann, Daniel L.
Bob-Egbe, Opetoritse
Rzepa, Henry S.
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Published in Angewandte Chemie: International Edition. 2017, vol. 56, no. 21, p. 5760-5764
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.
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Research group Groupe Bürgi
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MURRAY, James I. et al. Kinetic Resolution of 2-Substituted Indolines by N-Sulfonylation using an Atropisomeric 4-DMAP-N-oxide Organocatalyst. In: Angewandte Chemie: International Edition, 2017, vol. 56, n° 21, p. 5760-5764. https://archive-ouverte.unige.ch/unige:94104

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Deposited on : 2017-05-10

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