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- Title
Synthesis of Quinuclidines by Intramolecular Silver-Catalysed Amine Additions to Alkynes.
- Authors
Breman, Arjen C.; Ruiz‐Olalla, Andrea; van Maarseveen, Jan H.; Ingemann, Steen; Hiemstra, Henk
- Abstract
A new method has been developed for the synthesis of 2-alkylidenequinuclidines based on a silver triflate catalysed intramolecular hydroamination of 4-(prop-2-ynyl)piperidines. Monosubstituted piperidines reacted less efficiently than cis-disubstituted piperidines, and the reaction was selective for an alkyne moiety, even in the presence of a vinyl group at the 3-position. The hydroamination occurred readily with a terminal alkyne, as well as with an internal alkyne bearing an aliphatic or aromatic group at the terminal carbon atom. Using this silver-catalysed cyclization, a short procedure was developed for the relay synthesis of the cinchona alkaloids dihydroquinidine and dihydroquinine.
- Subjects
QUINUCLIDINES; HETEROCYCLIC compounds synthesis; MACROCYCLIC compound synthesis; TRIFLATE compounds; ENANTIOMERS
- Publication
European Journal of Organic Chemistry, 2014, Vol 2014, Issue 33, p7413
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201403099