3 years ago

Synthesis of Z- or E-Trisubstituted Allylic Alcohols and Ethers by Kinetically Controlled Cross-Metathesis with a Ru Catechothiolate Complex

Synthesis of Z- or E-Trisubstituted Allylic Alcohols and Ethers by Kinetically Controlled Cross-Metathesis with a Ru Catechothiolate Complex
Xiao Shen, Sebastian Torker, Zhenxing Liu, Chaofan Xu, Amir H. Hoveyda, Dongmin Xu
The first examples of kinetically controlled cross-metathesis reactions that generate Z- or E-trisubstituted alkenes are disclosed. Transformations are catalyzed by ≤6.0 mol % of a Ru catechothiolate complex and afford trisubstituted allylic alcohols and ethers in up to 81% yield and >98% stereoisomeric purity. The method has considerable scope, as olefins containing an alcohol, an aldehyde, an epoxide, a carboxylic acid, or an alkenyl group may be used. Mechanistic models that account for the observed levels and trends in efficiency and stereochemical control are provided, based on DFT studies.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b10010

DOI: 10.1021/jacs.7b10010

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