Stereoselective Synthesis of Multisubstituted α-fluoro-β-lactams

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Author(s): Atsushi Tarui, Yukiko Karuo, Kazuyuki Sato, Kentaro Kawai, Masaaki Omote*

Journal Name: Current Organic Chemistry

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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

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Article Details

(E-pub Ahead of Print)
DOI: 10.2174/1385272824666200221114707
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