Stereoselective Synthesis of Ezetimibe via Cross-Metathesis of Homoallylalcohols and α-Methylidene-β-Lactams
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- 作者：Marek Humpl ; Jiří Tauchman ; Nikola Topolovčan ; Jan Kretschmer ; Filip Hessler ; Ivana Císařová ; Martin Kotora ; Jan Veselý
- 刊名：Journal of Organic Chemistry
- 出版年：2016
- 出版时间：September 2, 2016
- 年：2016
- 卷：81
- 期：17
- 页码：7692-7699
- 全文大小：421K
- 年卷期：0
- ISSN：1520-6904
文摘
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.