Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 29, Pages 9969-9973Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201903860
Keywords
diversity-oriented synthesis; domino reactions; iso-Nazarov reaction; pericyclic reactions; polycyclization
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Funding
- Labex Charmmmat [ANR-11-LABX-0039]
- Labex SynOrg [ANR-11-LABX-0029]
- Agence Nationale de la Recherche (project ArDCo) [ANR-17-CE07-0050-03]
- Universite de Versailles Saint Quentin
- Universite Paris-Sud
- Centre National de la Recherche Scientifique (CNRS)
- Agence Nationale de la Recherche (ANR) [ANR-17-CE07-0050] Funding Source: Agence Nationale de la Recherche (ANR)
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We report an unprecedented domino polycyclization from readily available 2,4-dienals and cyclic a, b-unsaturated imines that is initiated by an iso-Nazarov reaction. This Bronsted acid promoted reaction enables the concomitant formation of four bonds, three cycles, and four contiguous stereogenic centers to yield elaborated structures in a single operation. A range of fused hexacyclic molecules is obtained in a highly diastereoselective manner.
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