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

被引：10

作者：

Ferreira, Jasmin ^{[1
]}

Rees-Jones, Sophie C. M. ^{[1
]}

Ramaotsoa, Valerie ^{[1
]}

Msutu, Ath'enkosi ^{[1
]}

Hunter, Roger ^{[1
]}

机构：

[1] Univ Cape Town, Dept Chem, ZA-7701 Cape Town, South Africa

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2016年 / 14卷 / 05期

基金：

新加坡国家研究基金会;

关键词：

NITROGEN-NITROGEN BOND; ASYMMETRIC-SYNTHESIS; ALPHA; ALPHA-DISUBSTITUTED ALDEHYDES; AMINATION REACTIONS; IONIC LIQUIDS; FUNCTIONALIZATION; AZODICARBOXYLATES; ORGANOCATALYSIS; CONSTRUCTION; REDUCTION;

D O I：

10.1039/c5ob02560e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：1545 / 1549

页数：5

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