Bis-paracyclophane N-heterocyclic carbene-ruthenium catalyzed asymmetric ketone hydrosilylation |
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Authors: | Chun Song Yudao Ma Wenhua Feng Qiang Chai |
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Affiliation: | a Chemistry College of Shandong University, Shanda South Road #27, Jinan, Shandong 250100, PR China b Brigham Young University, C100 BNSN, Department of Chemistry and Biochemistry, Provo, UT 84602-5700, USA |
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Abstract: | New chiral bis-paracyclophane N-heterocyclic carbene (NHC) ligands 1-3 have been explored for ruthenium catalyzed asymmetric hydrosilylation of ketones using diphenylsilane to give enantioenriched alcohols. These ligands provide for efficient asymmetric reduction in the presence of silver(I) triflate (1 mol %) at room temperature with high reactivity and selectivity. Acetophenone 4 was reduced with 1 mol % catalyst in 96% isolated yield, 97% ee. Following removal of the silyl ether, various alcohols 5 were obtained from aromatic ketones in high yield and selectivity. |
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Keywords: | Hydrosilylation Paracyclophane Asymmetric catalysis |
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