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Stereospecific decarboylative allylation of sulfones

Weaver, Jimmie D.
Ka, Being J.
Morris, David K.
Thompson, Ward H.
Tunge, Jon A.
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Abstract
Allyl sulfonyl acetic esters undergo highly stereospecific, palladium-catalyzed decarboxylative allylation. The reaction allows the stereospecific formation of tertiary homoallylic sulfones in high yield. In contrast to related reactions that proceed at -100 °C and require highly basic preformed organometallics, the decarboxylative coupling described herein occurs under mild non-basic conditions and requires no stoichiometric additives. Allylation of the intermediate α-sulfonyl anion is more rapid than racemization, leading to a highly enantiospecific process. DFT calculations indicate that the barrier for racemization is 9.9 kcal/mol and thus the barrier of allylation must be <9.9 kcal/mol.
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This document is the Accepted Manuscript version of a Published Work that appeared in final form in the Journal of the American Chemical Society, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://doi.org/10.1021/ja104196x.
Date
2010-09-08
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American Chemical Society
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Weaver, J. D., Ka, B. J., Morris, D. K., Thompson, W., & Tunge, J. A. (2010). Stereospecific decarboxylative allylation of sulfones. Journal of the American Chemical Society, 132(35), 12179–12181. http://doi.org/10.1021/ja104196x
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