Publication: Dual Catalysis in Enantioselective Oxidopyrylium-Based [5+2] Cycloadditions
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Date
2011
Published Version
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American Chemical Society
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Citation
Burns, Noah Z., Michael R. Witten, and Eric N. Jacobsen. 2011. Dual catalysis in enantioselective oxidopyrylium-based [5 + 2] cycloadditions. Journal of the American Chemical Society 133(37): 14578–14581.
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Abstract
A new method is reported for effecting catalytic enantioselective intramolecular [5+2] cycloadditions based on oxidopyrylium intermediates. The dual catalyst system consists of a chiral primary aminothiourea and a second achiral thiourea. Experimental evidence points to a new type of cooperative catalysis with each species being necessary to generate a reactive pyrylium ion pair which undergoes subsequent cycloaddition with high enantioselectivity.
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Keywords
cycloaddition reactions, organocatalysis, diastereoselective syntheses, enantioselective syntheses, multi-membered O,S-heterocycles
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