Gold(I)‐Catalysed Hydroarylation of Lactam‐Derived Enynes as an Entry to Tetrahydrobenzoquinolines

Gold(I)‐Catalysed Hydroarylation of Lactam‐Derived Enynes as an Entry to Tetrahydrobenzoquinolines

The gold(I)‐catalysed cyclization of N‐tosyl‐protected 5‐benzyl‐6‐((trimethylsilyl)ethynyl)‐1,2,3,4‐tetrahydropyridines, prepared by the Sonogashira coupling of lactam‐derived enol triflates, provides tetrahydrobenzo[g]quinolines whose skeleton represents a recurrent motif in natural compounds. The...

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Bibliographic Details
Published in:European journal of organic chemistry Vol. 2020; no. 6; pp. 646 - 653
Main Authors: Nejrotti, Stefano, Ghinato, Simone, Gini, Elena C, Scarpi, Dina, Occhiato, Ernesto G, Maranzana, Andrea, Prandi, Cristina
Format: Journal Article
Language:English
Published: Weinheim Wiley Subscription Services, Inc 01-02-2020
Subjects:
Amides
Gold
Organic compounds
Quinoline
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Summary:The gold(I)‐catalysed cyclization of N‐tosyl‐protected 5‐benzyl‐6‐((trimethylsilyl)ethynyl)‐1,2,3,4‐tetrahydropyridines, prepared by the Sonogashira coupling of lactam‐derived enol triflates, provides tetrahydrobenzo[g]quinolines whose skeleton represents a recurrent motif in natural compounds. The Au(I)‐catalysed reaction is carried out with (C6F5)3PAuCl/AgNTf2 as the catalyst system and proceeds via a 6‐exo‐dig cyclization to form an exocyclic double bond, which eventually isomerises to the aromatic tetrahydrobenzo[g]quinoline. The mode of cyclization is discussed and supported by DFT calculations.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201901599