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Lewis acid-catalyzed diastereoselective hydroarylation of benzylidene malonic esters.

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.

SUBMITTER: Duan S 

PROVIDER: S-EPMC2882201 | biostudies-literature | 2009 Jun

REPOSITORIES: biostudies-literature

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Lewis acid-catalyzed diastereoselective hydroarylation of benzylidene malonic esters.

Duan Shaofeng S   Jana Ranjan R   Tunge Jon A JA  

The Journal of organic chemistry 20090601 12

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. ...[more]

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