Functionalization of Csp-H bond—Sc(OTf)3-catalyzed domino 1,5-hydride shift/cyclization/Friedel-Crafts acylation reaction of benzylidene Meldrum’s acids |
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Authors: | Stuart J Mahoney Jon Hollinger |
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Institution: | Department of Chemistry, University of Waterloo, Waterloo, Ontario, Canada N2L 3G1 |
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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 tetracyclic core of tetrahydrobenzob]fluoren-11-ones. |
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