Reactivity of N-Boc-Protected Amino-Ynones in the Presence of Zinc Chloride: Formation of Acetylenic Cyclic Imines and Their Palladium Complexes - Université de Rennes Accéder directement au contenu
Article Dans Une Revue European Journal of Organic Chemistry Année : 2015

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

Résumé

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.

Domaines

Chimie

Dates et versions

hal-01174898 , version 1 (10-07-2015)

Identifiants

Citer

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, 2015, 2015 (22), pp.4868-4875. ⟨10.1002/ejoc.201500569⟩. ⟨hal-01174898⟩
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