Stereoselective Synthesis of Ezetimibe via Cross-Metathesis of Homoallylalcohols and α‑Methylidene-β-Lactams

Ru-catalyzed cross-metathesis (CM) reaction between β-arylated α-methylidene-β-lactams and terminal olefins was developed. The CM reaction is effectively catalyzed with Hoveyda–Grubbs second-generation catalyst affording corresponding α-alkylidene-β-aryl-β-lactams in good isolated yields (41–83%) wi...

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Bibliographic Details
Published in:Journal of organic chemistry 2016-09, Vol.81 (17), p.7692-7699
Main Authors: Humpl, Marek, Tauchman, Jiří, Topolovčan, Nikola, Kretschmer, Jan, Hessler, Filip, Císařová, Ivana, Kotora, Martin, Veselý, Jan
Format: Article
Language:English
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Summary:Ru-catalyzed cross-metathesis (CM) reaction between β-arylated α-methylidene-β-lactams and terminal olefins was developed. The CM reaction is effectively catalyzed with Hoveyda–Grubbs second-generation catalyst affording corresponding α-alkylidene-β-aryl-β-lactams in good isolated yields (41–83%) with exclusive Z-selectivity. The developed protocol was successfully applied for stereoselective preparation of Ezetimibe, the commercial cholesterol absorption inhibitor.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b01406