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Stereoselective synthesis of (1′S,3R,4R)-4-acetoxy-3-(2′-fluoro-1′-trimethylsilyloxyethyl)-2-azetidinone

✍ Scribed by Ivan Plantan; Michel Stephan; Uroš Urleb; Barbara Mohar

Publisher: Elsevier Science
Year: 2009
Tongue: French
Weight: 218 KB
Volume: 50
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2009.03.111

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✦ Synopsis

A stereoselective synthesis of (1 0 S,3R,4R)-4-acetoxy-3-(2 0 -fluoro-1 0 -trimethylsilyloxyethyl)-2-azetidinone as a new fluorine-containing intermediate towards b-lactams, is described. The synthetic key step relies upon the dynamic kinetic resolution (DKR) of ethyl 2-benzamidomethyl-4-fluoro-3-oxo-butanoate via asymmetric transfer hydrogenation catalyzed by [Ru(g 6 -arene)(S,S)-R 2 NSO 2 DPEN].

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