title: Direct and diastereoselective alkylation and aldol reactions of α-bromo-α-fluoro-β-lactams.
abstract: Herein, we describe the development of a method for the direct alkylation and aldol reaction of α-bromo-α-fluoro-β-lactams. This method provides facile access to a wide range of 3-alkyl- and 3-hydroxyalkyl-fluoro-β-lactams in good yields under mild conditions. The products were obtained with complete diastereoselectivity with regard to the relative configuration of the β-lactam ring at C3 and C4 positions. The reaction conditions were tolerant of a broad range of electrophiles, which highlights the overall scope and utility of this procedure.
authors.affiliation: Faculty of Pharmaceutical Sciences, Setsunan University, 45-1 Nagaotoge-cho, Hirakata, Osaka 573-0101 Japan.
authors.forename: Atsushi
authors.initials: A
authors.lastname: Tarui
authors.forename: Naoto
authors.initials: N
authors.lastname: Kawashima
authors.forename: Tetsuya
authors.initials: T
authors.lastname: Kawakita
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: D000478:Alkylation; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism; D047090:beta-Lactams / Q000737:chemistry*
chemical_list: D007659:Ketones; D047090:beta-Lactams