Chemoselective room temperature E1cB N-N cleavage of oxazolidinone hydrazides from enantioselective aldehyde α-hydrazination: synthesis of (+)-1,4-dideoxyallonojirimycin

Chemoselective room temperature E1cB N-N cleavage of oxazolidinone hydrazides from enantioselective aldehyde α-hydrazination: synthesis of (+)-1,4-dideoxyallonojirimycin

Room temperature E1cB N-N cleavage of oxazolidinone hydrazides via N-alkylation with diethyl bromomalonate and potassium or caesium carbonate as base in acetonitrile is presented. The new method has a much improved chemoselectivity, which is illustrated by a concise total synthesis of the piperidine...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic & biomolecular chemistry 2016-02, Vol.14 (5), p.1545-1549
Hauptverfasser: Ferreira, Jasmin, Rees-Jones, Sophie C M, Ramaotsoa, Valerie, Msutu, Ath'enkosi, Hunter, Roger
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes - chemistry
Hydrazines - chemistry
Imino Sugars - chemical synthesis
Imino Sugars - chemistry
Molecular Structure
Nitrogen - chemistry
Oxazolidinones - chemistry
Piperidines - chemical synthesis
Piperidines - chemistry
Stereoisomerism
Temperature
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:Room temperature E1cB N-N cleavage of oxazolidinone hydrazides via N-alkylation with diethyl bromomalonate and potassium or caesium carbonate as base in acetonitrile is presented. The new method has a much improved chemoselectivity, which is illustrated by a concise total synthesis of the piperidine iminosugar (+)-1,4-dideoxyallonojirimycin.
ISSN:1477-0520
1477-0539
DOI:10.1039/c5ob02560e