Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 24, Issue 10, Pages 2379-2383Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201800042
Keywords
1,3-dipoles; chiral phosphorous ligands; enantioselective catalysis; gold; heterocycles
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Funding
- China Scholarship Council
- Deutscher Akademischer Austausch Dienst (DAAD)
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The Au-I-catalyzed reaction of 2-(1-alkynyl)-2-alken-1-ones with azomethine imines regio- and diastereoselectively affords furo[3,4-d]tetrahydropyridazines in a tandem cyclization/intermolecular [3+3]-cycloaddition process under mild conditions. By employing a chiral gold catalyst (prepared in situ from a Taddol-derived phosphine-phosphite ligand, Me2SAuCl, and AgOTf) high yields and enantioselectivities (up to 94% yield, up to 96%ee) are obtained. The method provides an efficient modular route to substituted heterotricyclic furan derivatives and can be easily scaled up (using catalyst loads of only 0.15 mol%).
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