De novo designed contrasteric Diels-Alder reactions of 5-(2-oxazolynyl)-1,2,3,4,5-pentamethylcyclopentadiene |
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| Authors: | Masaru Ishida Satomi HirasawaSatoshi Inagaki |
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| Affiliation: | Department of Chemistry, Faculty of Engineering, Gifu University, Yanagido, Gifu 501-1193, Japan |
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| Abstract: | 5-(2-Oxazolynyl)cyclopentadiene was designed on the basis of the orbital mixing rule to react with dienophiles with highly contrasteric manner in Diels-Alder reactions. The design was validated by the synthesis and reactions of the corresponding pentamethyl derivative, 5-(2-oxazolynyl)-1,2,3,4,5-pentamethylcyclopentadiene, to afford the products with the ratios of syn/anti=89-93/11-7. |
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| Keywords: | cyclopentadienes Diels-Alder reactions molecular design stereocontrol substituent effects |
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