Synthetic Route to Chiral Indolines via Ring-Opening/C–N Cyclization of Activated 2-Haloarylaziridines

Ghorai, Manas K. ; Nanaji, Y. (2013) Synthetic Route to Chiral Indolines via Ring-Opening/C–N Cyclization of Activated 2-Haloarylaziridines The Journal of Organic Chemistry, 78 (8). pp. 3867-3878. ISSN 0022-3263

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Official URL: http://doi.org/10.1021/jo400287a

Related URL: http://dx.doi.org/10.1021/jo400287a

Abstract

A practical approach for the synthesis of 3-substituted indolines via regio- and stereoselective SN2-type ring-opening of 2-(2-halophenyl)-N-tosylaziridines with heteroatomic nucleophiles (O, N, and S) followed by palladium-catalyzed intramolecular C–N cyclization is reported in excellent yields (up to >99%) and enantiomeric excess (ee 99%).

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:117113
Deposited On:15 Apr 2021 07:58
Last Modified:15 Apr 2021 07:58

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