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dc.contributor.authorWeaver, Jimmie D.
dc.contributor.authorKa, Being J.
dc.contributor.authorMorris, David K.
dc.contributor.authorThompson, Ward H.
dc.contributor.authorTunge, Jon A.
dc.date.accessioned2017-06-06T16:22:19Z
dc.date.available2017-06-06T16:22:19Z
dc.date.issued2010-09-08
dc.identifier.citationWeaver, 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/ja104196xen_US
dc.identifier.urihttp://hdl.handle.net/1808/24381
dc.descriptionThis 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.en_US
dc.description.abstractAllyl 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.en_US
dc.publisherAmerican Chemical Societyen_US
dc.titleStereospecific decarboylative allylation of sulfonesen_US
dc.typeArticleen_US
kusw.kuauthorWeaver, Jimmie D.
kusw.kuauthorKa, Being J.
kusw.kuauthorMorris, David
kusw.kuauthorThompson, Ward H.
kusw.kuauthorTunge, Jon A.
kusw.kudepartmentChemistryen_US
dc.identifier.doi10.1021/ja104196xen_US
kusw.oaversionScholarly/refereed, author accepted manuscripten_US
kusw.oapolicyThis item meets KU Open Access policy criteria.en_US
dc.identifier.pmidPMC2935626en_US
dc.rights.accessrightsopenAccess


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