Kinetically controlled ring-closing metathesis: synthesis of a potential scaffold for 12-membered salicylic macrolides |
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Authors: | Matsuya Yuji Takayanagi Sho-ichi Nemoto Hideo |
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Institution: | Graduate School of Medicine and Pharmaceutical Sciemces, University of Toyama, Toyama, Japan. matsuya@pha.u-toyama.ac.jp |
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Abstract: | For the synthesis of a 12-membered salicylic macrolide scaffold, ring-closing metathesis (RCM) of a omega-diene compound was planned. The stereochemical outcome of the RCM reaction changed depending on the type of Ru catalyst that was used; a "first-generation" Grubbs catalyst produced exclusively the E isomer and "second-generation" catalysts provided a mixture of the E and Z isomers under kinetic control (not thermodynamic control). Considerations for the E/Z selectivity are described. |
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Keywords: | catalysis macrocycles metathesis ruthenium selectivity |
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