In:
European Journal of Organic Chemistry, Wiley, Vol. 2020, No. 6 ( 2020-02-14), p. 646-653
Abstract:
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 (C 6 F 5 ) 3 PAuCl/AgNTf 2 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.
Type of Medium:
Online Resource
ISSN:
1434-193X
,
1099-0690
DOI:
10.1002/ejoc.v2020.6
DOI:
10.1002/ejoc.201901599
Language:
English
Publisher:
Wiley
Publication Date:
2020
detail.hit.zdb_id:
1475010-7
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