1,5-Hydride-Shift-Triggered Cyclization for the Synthesis of Unsymmetric Julolidines

1,5-Hydride-Shift-Triggered Cyclization for the Synthesis of Unsymmetric Julolidines

Abstract Directly accessible 8-substituted tetrahydroquinolines undergo 1,5-hydride-shift-triggered cyclization to provide difficult to access julolidine derivatives in yields of 21–98% under scandium(III) triflate catalysis. Additionally, the scope of the reaction, several follow-up transformations...

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Veröffentlicht in:Synthesis (Stuttgart) 2021-12, Vol.53 (24), p.4689-4699
Hauptverfasser: Shirokova, Vasilissa V., Ikonnikova, Viktoria A., Solyev, Pavel N., Lushpa, Vladislav A., Korlyukov, Alexander A., Volodin, Alexander D., Baleeva, Nadezhda S., Baranov, Mikhail S., Mikhaylov, Andrey A.
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Sprache:eng
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Zusammenfassung:Abstract Directly accessible 8-substituted tetrahydroquinolines undergo 1,5-hydride-shift-triggered cyclization to provide difficult to access julolidine derivatives in yields of 21–98% under scandium(III) triflate catalysis. Additionally, the scope of the reaction, several follow-up transformations and a remarkable side process discovered during optimization of the conditions are highlighted.
ISSN:0039-7881
1437-210X
DOI:10.1055/a-1559-2728