4.7 Article

Lewis Acid-Catalyzed Diastereoselective Hydroarylation of Benzylidene Malonic Esters

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 12, Pages 4612-4614

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo900367g

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Funding

  1. National Institutes of Health [P50 GM069663]

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

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