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The Journal of organic chemistry

Synthetic route to chiral indolines via ring-opening/C-N cyclization of activated 2-haloarylaziridines.


PMID 23548056

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%).

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