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Chemoselective room temperature E1cB N–N cleavage of oxazolidinone hydrazides from enantioselective aldehyde α-hydrazination: synthesis of (+)-1,4-dideoxyallonojirimycin†
Jasmin Ferreira,Sophie C. M. Rees-Jones,Valerie Ramaotsoa,Ath'enkosi Msutu,Roger Hunter
Organic & Biomolecular Chemistry Pub Date : 12/18/2015 00:00:00 , DOI:10.1039/C5OB02560E
Abstract

Room temperature E1cB NN 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.

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