Buchumschlag

Addition of organometallic reagents to chiral N-methoxylactams: enantioselective syntheses of pyrrolidines and piperidines

Enantioselective iridium-catalyzed allylic substitutions were used to prepare N-allyl hydroxamic acid derivatives that were suitable for ring-closing metathesis, giving N-methoxylactams. Reactions of these derivatives with Grignard or organolithium compounds gave hemiaminals, which could be reduced...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Hauptverfasser: Jäkel, Mascha (VerfasserIn) , Qu, Jianping (VerfasserIn) , Schnitzer, Tobias (VerfasserIn) , Helmchen, Günter (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: 21 October 2013
In: Chemistry - a European journal
Year: 2013, Jahrgang: 19, Heft: 49, Pages: 16746-16755
ISSN:1521-3765
DOI:https://doi.org/10.1002/chem.201302735
Online-Zugang:Verlag, lizenzpflichtig, Volltext: https://doi.org/https://doi.org/10.1002/chem.201302735
Verlag, lizenzpflichtig, Volltext: https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/chem.201302735
Volltext
Verfasserangaben:Mascha Jäkel, Jianping Qu, Tobias Schnitzer, and Günter Helmchen
Beschreibung
Zusammenfassung:Enantioselective iridium-catalyzed allylic substitutions were used to prepare N-allyl hydroxamic acid derivatives that were suitable for ring-closing metathesis, giving N-methoxylactams. Reactions of these derivatives with Grignard or organolithium compounds gave hemiaminals, which could be reduced diastereoselectively via acyliminium intermediates to give cis-piperidines or cis-pyrrolidines with substituents in the 2,6- or 2,5-positions, respectively. In addition, compounds with a quaternary carbon center could be synthesized by corresponding reactions with potassium cyanide/AcOH. The procedures were applied in the syntheses of alkaloids (−)-209D and (+)-prosophylline.
Beschreibung:Gesehen am 24.03.2021
Beschreibung:Online Resource
ISSN:1521-3765
DOI:https://doi.org/10.1002/chem.201302735

Ähnliche Einträge