Journal of Organic Chemistry p. 2137 - 2141 (1987)
Update date:2022-07-30
Topics:
Curran, Dennis P.
Kim, Byeang Hyean
Piyasena, H. P.
Loncharich, R. J.
Houk, K. N.
Nitrile oxides undergo cycloadditions to several different chiral acrylates to give 0-56percent ?-facial stereoselectivity.In cases where stereoselectivity is significant, the structure of the major product is consistent with transition state with an s-cis conformation of the acrylate.Thermal Diels-Alder reactions of cyclopentadiene with these acrylates have also been studied, since the literature only gives results of catalyzed reactions.The major products are consistent with transition states which involve a small s-cis preference, by contrast to the substantial s-trans preferences required to explain results found by Oppolzer for the catalyzed reactions of the same acrylates.Model theoretical calculations also are in accord with these models, favoring an s-cis preference in the thermal reaction and an s-trans in the catalyzed.
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