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| - Organocatalytic Claisen Rearrangement: Theory and Experiment
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| Abstract
| - A combined computational and experimental study on the Claisen rearrangement of a 2-alkoxycarbonyl-substituted allyl vinyl ether in the presence of thioureas as potential noncovalent organocatalystshas been performed. DFT calculations employing different basis sets were utilized to predict a catalyticcycle for the thiourea-catalyzed Claisen rearrangement. The nature of the transition state in the presenceand absence of thioureas was studied in detail. Critical geometrical data of the transition state thatare indicators for the relative barrier height of the Claisen rearrangement are discussed. Although wedid observe a significant transition state stabilization, due to endergonic conformational changes andendergonic complexation the overall effect on the barrier is small, in accordance with experimentalresults.
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