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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.
π-Facial selectivity in Diels-Alder reactions of cyclopentadienes having C( O)YR substituents at the 5-positions was predicted on the basis of the orbital mixing rule and was substantiated experimentally. The selectivity was disclosed to be highly dependent on the relative orbital energy between π HOMO of the diene and n Y of the substituent.
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