Isotope effects for Lewis acid catalyzed Diels-Alder reactions. The experimental transition state
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2H and 13C kinetic isotope effects were determined for all positions on isoprene in its reactions with methyl vinyl ketone, ethyl acrylate, and acrolein catalyzed by Et2AlCl. The results are taken as supporting a highly asynchronous concerted [4+2] cycloaddition. Comparison of the experimental isotope effects with calculated values supports this conclusion and the accuracy of the calculated transition structure.
author list (cited authors)
Singleton, D. A., Merrigan, S. R., Beno, B. R., & Houk, K. N.