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...

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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
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container_title	Organic & biomolecular chemistry
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creator	Ferreira, Jasmin Rees-Jones, Sophie C M Ramaotsoa, Valerie Msutu, Ath'enkosi Hunter, Roger
description	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.
doi_str_mv	10.1039/c5ob02560e
format	Article
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source	MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection
subjects	Aldehydes - chemistry Hydrazines - chemistry Imino Sugars - chemical synthesis Imino Sugars - chemistry Molecular Structure Nitrogen - chemistry Oxazolidinones - chemistry Piperidines - chemical synthesis Piperidines - chemistry Stereoisomerism Temperature
title	Chemoselective room temperature E1cB N-N cleavage of oxazolidinone hydrazides from enantioselective aldehyde α-hydrazination: synthesis of (+)-1,4-dideoxyallonojirimycin
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