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

Murray James I. | Zendy; Flodén Nils J. | Zendy; Bauer Adriano | Zendy; Fessner Nico D. | Zendy; Dunklemann Daniel L. | Zendy; BobEgbe Opetoritse | Zendy; Rzepa Henry S. | Zendy; Bürgi Thomas | Zendy; Richardson Jeffery | Zendy; Spivey Alan C. | Zendy

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

Author(s) -

Murray James I.,

Flodén Nils J.,

Bauer Adriano,

Fessner Nico D.,

Dunklemann Daniel L.,

BobEgbe Opetoritse,

Rzepa Henry S.,

Bürgi Thomas,

Richardson Jeffery,

Spivey Alan C.

Publication year - 2017

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201700977

Subject(s) - chemistry , kinetic resolution , isopropyl , sulfonamide , catalysis , oxide , chloride , organic chemistry , resolution (logic) , medicinal chemistry , combinatorial chemistry , enantioselective synthesis , artificial intelligence , computer science

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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