title: Asymmetric synthesis of 2-substituted oxetan-3-ones via metalated SAMP/RAMP hydrazones.
abstract: 2-Substituted oxetan-3-ones can be prepared in good yields and enantioselectivities (up to 84% ee) by the metalation of the SAMP/RAMP hydrazones of oxetan-3-one, followed by reaction with a range of electrophiles that include alkyl, allyl, and benzyl halides. Additionally, both chiral 2,2- and 2,4-disubstituted oxetan-3-ones can be made in high ee (86-90%) by repetition of this lithiation/alkylation sequence under appropriately controlled conditions. Hydrolysis of the resultant hydrazones with aqueous oxalic acid provides the 2-substituted oxetan-3-ones without detectable racemization.
authors.affiliation: Department of Chemistry, University of Warwick , Gibbet Hill Road, Coventry CV4 7AL, United Kingdom.
authors.forename: Joanna V
authors.initials: JV
authors.lastname: Geden
authors.forename: Benjamin O
authors.initials: BO
authors.lastname: Beasley
authors.forename: Guy J
authors.initials: GJ
authors.lastname: Clarkson
authors.forename: Michael
authors.initials: M
authors.lastname: Shipman
mesh_terms: D004988:Ethers, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D006835:Hydrazones / Q000737:chemistry*; D008968:Molecular Conformation
chemical_list: D004988:Ethers, Cyclic; D006835:Hydrazones; C005287:oxetane