Deacylative allylation: allylic alkylation via retro-Claisen activation
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2011-09-21Article Version
Scholarly/refereed, author accepted manuscript
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A new method for allylic alkylation of a variety of relatively non-stabilized carbon nucleophiles is described herein. In this process of “deacylative allylation” the coupling partners, an allylic alcohol and a ketone pronucleophile, undergo in situ retro-Claisen activation to generate an allylic acetate and a carbanion. In the presence of palladium, these reactive intermediates undergo catalytic coupling to form a new C–C bond. In comparision to unimolecular decarboxylative allylation, a commonly utilized method for allylation of carbon anions, deacylative allylation is an intermolecular process. Moreover, deacylative allylation allows the direct coupling of readily available allylic alcohols. Lastly, the full utility of deacylative allylation is demonstrated by the rapid construction of a variety 1,6-heptadienes via 3-component couplings.
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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/ja205717f.
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Citation
Grenning, A. J., & Tunge, J. A. (2011). Deacylative allylation: allylic alkylation via retro-Claisen activation. Journal of the American Chemical Society, 133(37), 14785–14794. http://doi.org/10.1021/ja205717f
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