Acceleration effect of allylic hydroxy group on ring-closing enyne metathesis of terminal alkynes: scope and application to the synthesis of isofagomine |
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Authors: | Tatsushi Imahori |
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Institution: | Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan |
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Abstract: | An interesting allylic substituent effect on ring-closing enyne metathesis has been found. An allylic hydroxy group on enyne substrates accelerates ring-closing enyne metathesis of terminal alkynes. The reaction proceeds smoothly without ethylene atmosphere and/or more reactive newer generation Ru-carbene catalysts, which are generally necessary to promote the reaction. This efficient reaction was applied to the synthesis of isofagomine. |
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