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Stereoselective Synthesis of Multisubstituted α-fluoro-β-lactams

Author(s):

Atsushi Tarui, Yukiko Karuo, Kazuyuki Sato, Kentaro Kawai and Masaaki Omote*   Pages 1 - 10 ( 10 )

Abstract:


β-Lactams, structures found in β-lactam antibiotics, are the structurally distorted cyclic compounds being subject to nucleophilic acyl substitution reaction. α-Fluorination of β-lactams is a simple and expedient approach to control the reactivity of β-lactam ring toward nucleophilic attack, which would hopefully lead to new design of future antibiotics. From the viewpoint of obtaining multisubstituted α-fluoro-β-lactams, α-bromo-α-fluoro-β-lactams are considered as key compounds for structure functionalization, including nucleophilic substitution reaction, aldol-type reaction and metal-catalyzed cross-coupling reaction. All the reactions can be conducted smoothly to afford a variety of multisubstituted α-fluoro-β-lactams. During the course of the examination, chiral α,α-difluoro-β-lactams and α-bromo-α-fluoro-β-lactams are successfully obtained which are considered potent precursors for making stereocontrolled multisubstituted α-fluoro-β-lactams.

Keywords:

fluorine, β-lactam, β-amino acid, stereoselective synthesis, cross-coupling, Reformatsky reaction

Affiliation:

Faculty of Pharmaceutical Sciences, Setsunan University, Faculty of Pharmaceutical Sciences, Setsunan University, Faculty of Pharmaceutical Sciences, Setsunan University, Faculty of Pharmaceutical Sciences, Setsunan University, Faculty of Pharmaceutical Sciences, Setsunan University



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