Efficient Enantioselective Synthesis of Functionalized Tetrahydropyrans by Ru-Catalyzed Asymmetric Ring-Opening Metathesis/Cross-Metathesis (AROM/CM)

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• 作者：Dennis G. Gillingham ; Osamu Kataoka ; Steven B. Garber ; and Amir H. Hoveyda
• 刊名：Journal of the American Chemical Society
• 出版年：2004
• 出版时间：October 6, 2004
• 年：2004
• 卷：126
• 期：39
• 页码：12288 - 12290
• 全文大小：88K
• 年卷期：v.126,no.39(October 6, 2004)
• ISSN：1520-5126

文摘

An efficient method for enantioselective synthesis of highly functionalized pyrans (up to 98% ee) through Ru-catalyzed asymmetric ring-opening metathesis/cross-metathesis is described. Reactions are promoted by a recyclable chiral Ru-chloride or a new chiral Ru-iodide complex; the latter catalyst is less efficient but gives rise to significantly higher levels of enantioselectivity. Catalytic reactions can be performed in undistilled solvent and with a wide range of substrates, including those that contain secondary and tertiary alcohols. Representative regioselective functionalizations that highlight the utility of the catalytic method are also presented.