Lewis acid catalyzed diastereoselective [3+4]-annulation of donor–acceptor cyclopropanes with anthranils: synthesis of tetrahydro-1-benzazepine derivatives
| Autor: | Dao-Ming Wang, Peng-Fei Xu, Zhe-Hao Wang, Yong-Chun Luo, Huan-Huan Zhang |
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| Rok vydání: | 2017 |
| Předmět: |
Annulation
Nucleophilic addition 010405 organic chemistry Chemistry Stereochemistry Metals and Alloys Aromatization General Chemistry 010402 general chemistry 01 natural sciences Catalysis 0104 chemical sciences Surfaces Coatings and Films Electronic Optical and Magnetic Materials Benzazepine Cyclopropane chemistry.chemical_compound Materials Chemistry Ceramics and Composites Lewis acids and bases Donor acceptor |
| Zdroj: | Chemical Communications. 53:8521-8524 |
| ISSN: | 1364-548X 1359-7345 |
| DOI: | 10.1039/c7cc04239f |
| Popis: | A Lewis acid catalyzed [3+4]-annulation reaction between cyclopropane 1,1-diesters and anthranils has been developed. This annulation consists of a reaction sequence involving ring-opening/aromatization/nucleophilic addition. Thereinto, aromatization is the driving force for this annulation. Using this reaction, a series of 8-oxa-1-azabicyclo[3.2.1]octanes can be prepared conveniently with excellent diastereoselectivity. |
| Databáze: | OpenAIRE |
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