title: Organolithium-induced alkylative ring opening of aziridines: synthesis of unsaturated amino alcohols and ethers.
abstract: Organolithium-induced alkylative ring opening of N-sulfonyl-protected aziridinyl ethers is described. The reactions were efficiently carried out with a variety of organolithiums, providing a promising new strategy to unsaturated amino alcohols and ethers. Cis- and trans-1,4-dimethoxybut-2-ene-derived aziridines were prepared, and their propensity to undergo organolithium- induced alkylative desymmetrization is detailed. Use of a single enantiomer of the latter aziridine provides a route to enantiopure unsaturated amino ethers.
authors.affiliation: Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, United Kingdom.
authors.forename: David M
authors.initials: DM
authors.lastname: Hodgson
authors.forename: Bogdan
authors.initials: B
authors.lastname: Stefane
authors.forename: Timothy J
authors.initials: TJ
authors.lastname: Miles
authors.forename: Jason
authors.initials: J
authors.lastname: Witherington
mesh_terms: D000478:Alkylation; D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D001388:Aziridines / Q000737:chemistry*; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D008094:Lithium / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000605:Amino Alcohols; D001388:Aziridines; D004987:Ethers; D009942:Organometallic Compounds; D008094:Lithium