title: Enantioselective synthesis of α,α-difluoro-β-lactams using amino alcohol ligands.
abstract: A practical and highly enantioselective Reformatsky reaction of ethyl bromodifluoroacetate with imines using a cheap and commercially available amino alcohol ligand is described. A variety of α,α-difluoro-β-lactams were obtained in up to 74% yield with high enantioselectivity in excess of 99% ee. The use of ethyl bromodifluoroacetate provides for ease of operation because of the inherent chemical stability of this reagent.
authors.affiliation: Faculty of Pharmaceutical Sciences, Setsunan University, 45-1 Nagaotoge-cho, Hirakata, Osaka 573-0101, Japan. aando@pharm.setsunan.ac.jp.
authors.forename: Atsushi
authors.initials: A
authors.lastname: Tarui
authors.forename: Takeshi
authors.initials: T
authors.lastname: Ikebata
authors.forename: Kazuyuki
authors.initials: K
authors.lastname: Sato
authors.forename: Masaaki
authors.initials: M
authors.lastname: Omote
authors.forename: Akira
authors.initials: A
authors.lastname: Ando
mesh_terms: D000605:Amino Alcohols / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D013237:Stereoisomerism; D047090:beta-Lactams / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000605:Amino Alcohols; D008024:Ligands; D047090:beta-Lactams