Synthesis of Z- or E-Trisubstituted Allylic Alcohols and Ethers by Kinetically Controlled Cross-Metathesis with a Ru Catechothiolate Complex
Chaofan Xu, Zhenxing Liu, Sebastian Torker, Xiao Shen, Dongmin Xu and Amir H. Hoveyda*
*Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, United States, Email: amir.hoveydabc.edu
C. Xu, Z. Liu, S. Torker, X. Shen, D. Xu, A. H. Hoveyda, J. Am. Chem. Soc., 2017, 139, 15640-15643.
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A Ru catechothiolate complex catalyzes kinetically controlled cross-metathesis reactions to afford trisubstituted allylic alcohols and ethers in up to 81% yield and >98% stereoisomeric purity. The method has considerable scope and tolerates various functional groups. Mechanistic models that account for the observed levels and trends in efficiency and stereochemical control are provided, based on DFT studies.
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