Tandem Olefin Metathesis/Oxidative Cyclization: Synthesis of Tetrahydrofuran Diols from Simple Olefins

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• 作者：Peter K. Dornan ; Daniel Lee ; Robert H. Grubbs
• 刊名：Journal of the American Chemical Society
• 出版年：2016
• 出版时间：May 25, 2016
• 年：2016
• 卷：138
• 期：20
• 页码：6372-6375
• 全文大小：423K
• 年卷期：0
• ISSN：1520-5126

文摘

A tandem olefin metathesis/oxidative cyclization has been developed to synthesize 2,5-disubstituted tetrahydrofuran (THF) diols in a stereocontrolled fashion from simple olefin precursors. The ruthenium metathesis catalyst is converted into an oxidation catalyst in the second step and is thus responsible for both catalytic steps. The stereochemistry of the 1,5-diene intermediate can be controlled through the choice of catalyst and the type of metathesis conducted. This olefin stereochemistry then controls the THF diol stereochemistry through a highly stereospecific oxidative cyclization.