Amidopalladation of Alkoxyallenes Applied in the Synthesis of an Enantiopure 1-Ethylquinolizidine Frog Alkaloid

A palladium-catalyzed amidation of alkoxyallenes has been developed for the construction of linear allylic N,O-acetals under basic conditions involving (cyclic) amides, sulfonamides, carbamates, and amidophosphates. Application of the methodology provided access to the enantiopure 1-ethylquinolizidi...

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Journal of the American Chemical Society 2004-04, Vol.126 (13), p.4100-4101
Hauptverfasser:	Kinderman, Sape S, de Gelder, René, van Maarseveen, Jan H, Schoemaker, Hans E, Hiemstra, Henk, Rutjes, Floris P. J. T
Format:	Artikel
Sprache:	eng
Schlagworte:	Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Organic chemistry Preparations and properties
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

Beschreibung
Zusammenfassung:	A palladium-catalyzed amidation of alkoxyallenes has been developed for the construction of linear allylic N,O-acetals under basic conditions involving (cyclic) amides, sulfonamides, carbamates, and amidophosphates. Application of the methodology provided access to the enantiopure 1-ethylquinolizidine structural motif, which is a key synthon in the synthesis of the naturally occurring poisonous frog quinolizidine 233A and derivatives such as the 1-epi-isomer of quinolizidine 207I.
ISSN:	0002-7863 1520-5126
DOI:	10.1021/ja039919j