title: Chemoselective room temperature E1cB N-N cleavage of oxazolidinone hydrazides from enantioselective aldehyde α-hydrazination: synthesis of (+)-1,4-dideoxyallonojirimycin.
abstract: 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.
authors.affiliation: Chemistry Department, University of Cape Town, Rondebosch 7701, Cape Town, South Africa. Roger.Hunter@uct.ac.za.
authors.forename: Jasmin
authors.initials: J
authors.lastname: Ferreira
authors.affiliation: Chemistry Department, University of Cape Town, Rondebosch 7701, Cape Town, South Africa. Roger.Hunter@uct.ac.za.
authors.forename: Sophie C M
authors.initials: SC
authors.lastname: Rees-Jones
authors.affiliation: Chemistry Department, University of Cape Town, Rondebosch 7701, Cape Town, South Africa. Roger.Hunter@uct.ac.za.
authors.forename: Valerie
authors.initials: V
authors.lastname: Ramaotsoa
authors.affiliation: Chemistry Department, University of Cape Town, Rondebosch 7701, Cape Town, South Africa. Roger.Hunter@uct.ac.za.
authors.forename: Ath'enkosi
authors.initials: A
authors.lastname: Msutu
authors.affiliation: Chemistry Department, University of Cape Town, Rondebosch 7701, Cape Town, South Africa. Roger.Hunter@uct.ac.za.
authors.forename: Roger
authors.initials: R
authors.lastname: Hunter
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D006834:Hydrazines / Q000737:chemistry*; D050111:Imino Sugars / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D023303:Oxazolidinones / Q000737:chemistry*; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013696:Temperature
chemical_list: C000611469:1,4-dideoxyallonojirimycin; D000447:Aldehydes; D006834:Hydrazines; D050111:Imino Sugars; D023303:Oxazolidinones; D010880:Piperidines; D009584:Nitrogen