Lewis acid-catalyzed diastereoselective hydroarylation of benzylidene malonic esters.
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.
Duan
Shaofeng
S
Department of Chemistry, 1251 Wescoe Hall Drive, 2010 Malott Hall, and the KU Chemical Methodologies and Library Development Center of Excellence, The University of Kansas, Lawrence, Kansas 66045-7582, USA.
Jana
Ranjan
R
Tunge
Jon A
JA
D001597:Benzylidene Compounds / Q000737:chemistry*; D002384:Catalysis; D003374:Coumarins / Q000138:chemical synthesis*; D004952:Esters / Q000737:chemistry; D008314:Malonates / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry; D013237:Stereoisomerism
D001597:Benzylidene Compounds; D003374:Coumarins; D004952:Esters; D008314:Malonates; D010636:Phenols; C030290:malonic acid