Gold‐Catalyzed [4+2] Annulation/Cyclization Cascades of Benzisoxazoles with Propiolate Derivatives to Access Highly Oxygenated Tetrahydroquinolines. (31st August 2017)

• Record Type: Journal Article
• Authors: Sahani, Rajkumar Lalji; Liu, Rai‐Shung
• Is Part Of: Angewandte Chemie. Volume 129:Number 41(2017)
• Page Start: 12910
• Page End: 12914
• Publication Date: 2017-08-31
• Subjects: Anellierungen -- Gold -- Heterocyclen -- Silber -- Synthesemethoden; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201707423
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: This work describes gold‐catalyzed annulations of electron‐deficient alkynes with benzisoxazoles to yield quinoline oxides chemoselectively. Chemical functionalizations of these resulting azacyclic compounds afforded various oxygenated tetrahydroquinolines which are present as the cores of many bioactive molecules. With the same reactants, a new relay catalysis using gold and zinc(II) catalysts affords highly oxygenated tetrahydroquinoline derivatives stereoselectively. Abstract : Katalytische Staffel : Goldkatalysierte Kaskaden aus [4+2]‐Anellierung und Cyclisierung zwischen elektronenarmen Alkinen und Benzisoxazolen führen chemoselektiv zu Chinolinoxiden. Dieselben Reaktionspartner verbinden sich in einer Gold‐Zink(II)‐Staffelkatalyse stereoselektiv zu hoch oxygenierten Tetrahydrochinolin‐Derivaten. Tf=Trifluormethansulfonyl.