Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 3, Pages 1134-1138Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201911761
Keywords
electrocyclization; hexafluoroisopropanol; Lewis acid; medium-size N-heterocycles; tetrahydrobenzo[b]azepines
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Funding
- CNRS
- Universite Paris-Sud
- Universite Paris-Saclay
- ANR [ANR-17-CE07-0003-02 ALCACAT]
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Herein, we report the preparation of bridged tetrahydrobenzo[b]azepines, which was accomplished through an aza-Piancatelli cyclization/Michael addition sequence in a one-pot fashion from readily available precursors. It is noteworthy that a general method to access these scaffolds was hitherto unprecedented. Additionally, the multifaceted aspects of this process have been exemplified through its application to the synthesis of 2-azabicyclo[3.2.1]octanes and bridged tetrahydrobenzo[b]oxepines, along with post-derivatizations.
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