Lewis acid-catalyzed diastereoselective hydroarylation of benzylidene malonic esters

Duan, Shaofeng; Jana, Ranjan; Tunge, Jon A.

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Issue Date

2009-06-19

Author

Duan, Shaofeng

Jana, Ranjan

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 the Journal of Organic Chemistry, 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/jo900367g.

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Abstract

Herein we report that simple Lewis acids catalyze the hydroarylation of benzylidene malonates with phenols. Ultimately, 3,4-disubstituted dihydrocoumarins are obtained via a hydroarylation-lactonization sequence. Moreover, the dihydrocoumarins are formed with a high degree of diastereoselectivity favoring the trans stereoisomer.

Citation

Duan, S., Jana, R., & Tunge, J. A. (2009). Lewis acid-catalyzed diastereoselective hydroarylation of benzylidene malonic esters. The Journal of Organic Chemistry, 74(12), 4612–4614. http://doi.org/10.1021/jo900367g

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