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N-heterocyclic carbene (NHC)-catalyzed/Lewis acid mediated conjugate umpolung of alkynyl aldehydes for the synthesis of butenolides: a formal [3+2] annulation

N-heterocyclic carbene (NHC)-catalyzed/Lewis acid mediated conjugate umpolung of alkynyl aldehydes for the synthesis of butenolides: a formal [3+2] annulation

Chemistry 19(13): 4146-4150

Reverse to success! A new formal [3+2] annulation reaction combining alkynyl aldehydes and β,γ-unsaturated α-ketoesters has been disclosed by using a NHC-catalyzed/Lewis acid mediated strategy. This cooperative catalysis strategy first allows the "allenolate" intermediate as a nucleophilic synthon at the β-position to react with activated electrophilic reagents by an addition reaction as the key C-C bond-forming step.

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Accession: 054529351

Download citation: RISBibTeXText

PMID: 23447469

DOI: 10.1002/chem.201204386

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