Yb (OTf) 3-catalyzed reactions of 5-alkylidene Meldrum's acids with phenols: one-pot assembly of 3, 4-dihydrocoumarins, 4-chromanones, coumarins, and chromones

…, AM Dumas, BA Kuropatwa, NR Malhotra…

Index: Fillion, Eric; Dumas, Aaron M.; Kuropatwa, Bryan A.; Malhotra, Neil R.; Sitler, Tamsyn C. Journal of Organic Chemistry, 2006 , vol. 71, # 1 p. 409 - 412

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Citation Number: 72

Abstract

The Yb (OTf) 3-catalyzed annulation reactions of phenols with 5-alkylidene Meldrum's acids enabled the synthesis of structurally diverse heterocycles in high isolated yields. A series of 4-substituted 3, 4-dihydrocoumarins, 2, 2-disubstituted 4-chromanones, coumarins, and 2- substituted chromones were readily and efficiently assembled, including the naturally occurring coumarins citropten, scoparone, and ayapin. Addition of phenols to ...