Mechanistic origin of the stereodivergence in decarboxylative allylation

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Issue Date
2010-07-02Author
Chattopadhyay, Kalicharan
Jana, Ranjan
Day, Victor W.
Douglas, Justin T.
Tunge, Jon A.
Publisher
American Chemical Society
Type
Article
Article Version
Scholarly/refereed, author accepted manuscript
Rights
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/ol101042x.
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Show full item recordAbstract
A stereochemical test has been used to probe the mechanism of decarboxylative allylation. This probe suggests that the mechanism of DcA reactions can change based on the substitution pattern at the α-carbon of the nucleophile, however reaction via stabilized malonate nucleophiles is the lower energy pathway. Lastly, this mechanistic proposal has predictive power and can be used to explain chemoselectivities in decarboxylative reactions that were previously confounding.
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Citation
Chattopadhyay, K., Jana, R., Day, V. W., Douglas, J. T., & Tunge, J. A. (2010). Mechanistic origin of the stereodivergence in decarboxylative allylation. Organic Letters, 12(13), 3042–3045. http://doi.org/10.1021/ol101042x
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