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Stereoselective Synthesis of Multisubstituted α-fluoro-β-lactams

[ Vol. 24 , Issue. 18 ]

Author(s):

Atsushi Tarui, Yukiko Karuo, Kazuyuki Sato, Kentaro Kawai and Masaaki Omote*   Pages 2169 - 2180 ( 12 )

Abstract:


β-Lactams, found in β -lactam antibiotics, are the structurally distorted cyclic compounds being subjected 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 the 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 crosscoupling 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-β-fluoro-α-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, Hirakata, Osaka 573-0101, Faculty of Pharmaceutical Sciences, Setsunan University, Hirakata, Osaka 573-0101, Faculty of Pharmaceutical Sciences, Setsunan University, Hirakata, Osaka 573-0101, Faculty of Pharmaceutical Sciences, Setsunan University, Hirakata, Osaka 573-0101, Faculty of Pharmaceutical Sciences, Setsunan University, Hirakata, Osaka 573-0101

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