Changing Reaction Pathways of the Dimerization of 2‑Formylcinnamates by N‑Heterocyclic Carbene/Lewis Acid Cooperative Catalysis: An Unusual Cleavage of the Carbon–Carbon Bond

Catalyzed by a triazole carbene, the dimerization of 2-formylcinnamates underwent benzoin condensation followed by intramolecular oxa-Michael addition to afford isochromeno[4,3-c]isochromene products. Under the catalysis of a combination of triazole carbene and Ti(OPr-i)4 catalysts, the dimerization...

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Bibliographic Details
Published in:Organic letters 2014-11, Vol.16 (21), p.5520-5523
Main Authors: Dang, Hai-Yan, Wang, Zi-Tian, Cheng, Ying
Format: Article
Language:English
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Summary:Catalyzed by a triazole carbene, the dimerization of 2-formylcinnamates underwent benzoin condensation followed by intramolecular oxa-Michael addition to afford isochromeno[4,3-c]isochromene products. Under the catalysis of a combination of triazole carbene and Ti(OPr-i)4 catalysts, the dimerization reaction of 2-formylcinnamates proceeded through a completely different route to furnish the formation of isochromenone derivatives with the elimination of an acetate moiety.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol502791s