4.7 Article

Enantioselective Synthesis of 2-Bromomethyl Indolines via BINAP(S)-Catalyzed Bromoaminocyclization of Allyl Aniline

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 359, Issue 14, Pages 2499-2508

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201700106

Keywords

enantioselective synthesis; indolines; bromoaminocyclization; allyl aniline; N-bromosuccinimide (NBS); BINAP(S)

Funding

  1. National Natural Science Foundation of China [21572154]

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An enantioselective bromoamination of allyl aniline with N-bromosuccinimide (NBS) catalyzed by BINAP(S) (BINAP monosulfide) is described. This protocol could provide a range of chiral 2-bromomethyl indolines in good to excellent yields with up to 87% ee. Furthermore, the resulting chiral 2-bromomethyl indolines could be easily converted into synthetically useful chiral building blocks.

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