Tetrahedron Letters

Functionalization of Csp 3–H bond—Sc (OTf) 3-catalyzed domino 1, 5-hydride shift/cyclization/Friedel–Crafts acylation reaction of benzylidene Meldrum's acids

SJ Mahoney, DT Moon, J Hollinger, E Fillion

Index: Mahoney, Stuart J.; Moon, David T.; Hollinger, Jon; Fillion, Eric Tetrahedron Letters, 2009 , vol. 50, # 33 p. 4706 - 4709

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Citation Number: 45

Abstract

Under Sc (OTf) 3 catalysis, benzylidene Meldrum's acids bearing a tethered p- methoxyphenethyl group were observed to undergo a [1, 5]-hydride shift/cyclization at room temperature, representing a mild Csp3–H bond functionalization. The resulting spiro Meldrum's acid intermediates then underwent intramolecular Friedel–Crafts acylation, completing the one-pot, domino reaction. The reported protocol generates the 6-6-5-6 ...