Skip to Main content Skip to Navigation
Journal articles

Reactivity of N-Boc-Protected Amino-Ynones in the Presence of Zinc Chloride: Formation of Acetylenic Cyclic Imines and Their Palladium Complexes

Abstract : Amino-ynones can be seen as precursors of various heterocyclic rings. Although γ-amino-ynones have been used to prep. exocyclic vinylogous amides in the presence of Bronsted acids, we describe here the use of zinc chloride as a weak Lewis acid for their conversion into acetylenic cyclic imines. This reaction, which was attempted for a diverse range of γ-amino-ynones, proved to be robust and efficient in most cases and was easily extended to δ-amino-ynones to yield various acetylenic cyclic imines. Depending on the workup procedure, the latter compds. could be isolated either as free org. compds. or as zinc complexes. The ability of these cyclic imines to form complexes with palladium is also reported.
Document type :
Journal articles
Complete list of metadatas

https://hal-univ-rennes1.archives-ouvertes.fr/hal-01174898
Contributor : Laurent Jonchère <>
Submitted on : Friday, July 10, 2015 - 10:39:59 AM
Last modification on : Thursday, March 5, 2020 - 2:02:10 PM

Links full text

Identifiers

Citation

Huy-Dinh Vu, Jacques Renault, Thierry Roisnel, Clémence Robert, Philippe Jehan, et al.. Reactivity of N-Boc-Protected Amino-Ynones in the Presence of Zinc Chloride: Formation of Acetylenic Cyclic Imines and Their Palladium Complexes. European Journal of Organic Chemistry, Wiley-VCH Verlag, 2015, 2015 (22), pp.4868-4875. ⟨10.1002/ejoc.201500569⟩. ⟨hal-01174898⟩

Share

Metrics

Record views

148