Mechanistic origin of the stereodivergence in decarboxylative allylation

Chattopadhyay, Kalicharan; Jana, Ranjan; Day, Victor W.; Douglas, Justin T.; Tunge, Jon A.

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Issue Date

2010-07-02

Author

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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Abstract

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.

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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