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

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

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‐bromometh...

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Veröffentlicht in:Advanced synthesis & catalysis 2017-07, Vol.359 (14), p.2499-2508
Hauptverfasser: Yu, Sheng‐Nan, Li, Yin‐Long, Deng, Jun
Format: Artikel
Sprache:eng
Schlagworte:
allyl aniline
Aniline
BINAP(S)
bromoaminocyclization
Chemical synthesis
enantioselective synthesis
Heterocyclic compounds
indolines
N-bromosuccinimide (NBS)
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Zusammenfassung: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.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201700106