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Stereospecific decarboylative allylation of sulfones
dc.contributor.author | Weaver, Jimmie D. | |
dc.contributor.author | Ka, Being J. | |
dc.contributor.author | Morris, David K. | |
dc.contributor.author | Thompson, Ward H. | |
dc.contributor.author | Tunge, Jon A. | |
dc.date.accessioned | 2017-06-06T16:22:19Z | |
dc.date.available | 2017-06-06T16:22:19Z | |
dc.date.issued | 2010-09-08 | |
dc.identifier.citation | 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 | en_US |
dc.identifier.uri | http://hdl.handle.net/1808/24381 | |
dc.description | 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. | en_US |
dc.description.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. | en_US |
dc.publisher | American Chemical Society | en_US |
dc.title | Stereospecific decarboylative allylation of sulfones | en_US |
dc.type | Article | en_US |
kusw.kuauthor | Weaver, Jimmie D. | |
kusw.kuauthor | Ka, Being J. | |
kusw.kuauthor | Morris, David | |
kusw.kuauthor | Thompson, Ward H. | |
kusw.kuauthor | Tunge, Jon A. | |
kusw.kudepartment | Chemistry | en_US |
dc.identifier.doi | 10.1021/ja104196x | en_US |
kusw.oaversion | Scholarly/refereed, author accepted manuscript | en_US |
kusw.oapolicy | This item meets KU Open Access policy criteria. | en_US |
dc.identifier.pmid | PMC2935626 | en_US |
dc.rights.accessrights | openAccess |