Ring Opening/C–N Cyclization of Activated Aziridines with Carbon Nucleophiles: Highly Diastereo- and Enantioselective Synthesis of Tetrahydroquinolines

Ring Opening/C–N Cyclization of Activated Aziridines with Carbon Nucleophiles: Highly Diastereo- and Enantioselective Synthesis of Tetrahydroquinolines

A simple strategy for the synthesis of substituted tetrahydroquinolines through regio- and stereoselective ring opening of N-tosyl aziridines with carbon nucleophiles generated from 2-(bromoaryl)acetonitriles followed by palladium-catalyzed intramolecular C–N cyclization is reported in excellent yie...

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Veröffentlicht in:Organic letters 2011-08, Vol.13 (16), p.4256-4259
Hauptverfasser: Ghorai, Manas K, Nanaji, Y, Yadav, A. K
Format: Artikel
Sprache:eng
Schlagworte:
Aziridines - chemistry
Carbon - chemistry
Cyclization
Molecular Structure
Nitrogen - chemistry
Quinolines - chemistry
Stereoisomerism
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Zusammenfassung:A simple strategy for the synthesis of substituted tetrahydroquinolines through regio- and stereoselective ring opening of N-tosyl aziridines with carbon nucleophiles generated from 2-(bromoaryl)acetonitriles followed by palladium-catalyzed intramolecular C–N cyclization is reported in excellent yields (up to >99%) and stereoselectivity (ee and de up to >99%).
ISSN:1523-7060
1523-7052
DOI:10.1021/ol2016077