Enantioselective Intramolecular Benzylic CH Bond Amination: Efficient Synthesis of Optically Active Benzosultams

Enantioselective Intramolecular Benzylic CH Bond Amination: Efficient Synthesis of Optically Active Benzosultams

'Salen' along: The iridium(III)–salen complex 1 efficiently catalyzes the title reaction of 2‐ethylbenzenesulfonyl azides to give five‐membered sultams with high enantioselectivity. Other 2‐alkyl‐substitued substrates lead to five‐ and six‐membered sultams with high enantioselectivity; the...

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Veröffentlicht in:Angewandte Chemie International Edition 2011-10, Vol.50 (42), p.9884-9887
Hauptverfasser: Ichinose, Masami, Suematsu, Hidehiro, Yasutomi, Yoichi, Nishioka, Yota, Uchida, Tatsuya, Katsuki, Tsutomu
Format: Artikel
Sprache:eng
Schlagworte:
Amination
CH amination
heterocycles
homogeneous catalysis
iridium
Molecular Structure
Optical Phenomena
Stereoisomerism
Sulfonamides - chemical synthesis
Sulfonamides - chemistry
synthetic methods
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Beschreibung
Zusammenfassung:'Salen' along: The iridium(III)–salen complex 1 efficiently catalyzes the title reaction of 2‐ethylbenzenesulfonyl azides to give five‐membered sultams with high enantioselectivity. Other 2‐alkyl‐substitued substrates lead to five‐ and six‐membered sultams with high enantioselectivity; the regioselectivity depends upon the substrate and the catalyst used. EDG=electron‐donating group.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201101801