Construction of tetralin and chromane cores by the Lewis acid promoted ring-opening cyclization of cyclopropyl methanesulfonates
[Display omitted] Rearrangement of cyclopropyl methanesulfonates to allylic carbocations was employed for the construction of tetralin and chromate bicyclic cores. We found that this transformation proceeds efficiently and rapidly at room temperature in the presence of dimethylaluminium triflate ser...
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| Published in: | Tetrahedron letters Vol. 104; p. 154025 |
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| Main Authors: | , , , |
| Format: | Journal Article |
| Language: | English |
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17-08-2022
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| Abstract | [Display omitted]
Rearrangement of cyclopropyl methanesulfonates to allylic carbocations was employed for the construction of tetralin and chromate bicyclic cores. We found that this transformation proceeds efficiently and rapidly at room temperature in the presence of dimethylaluminium triflate serving as a non-nucleophilic Lewis acid. The reaction begins with the cyclopropanol ring-opening and follows by the Friedel-Crafts cyclization of the resulting cationic intermediate with a pendant aromatic ring. |
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| AbstractList | [Display omitted]
Rearrangement of cyclopropyl methanesulfonates to allylic carbocations was employed for the construction of tetralin and chromate bicyclic cores. We found that this transformation proceeds efficiently and rapidly at room temperature in the presence of dimethylaluminium triflate serving as a non-nucleophilic Lewis acid. The reaction begins with the cyclopropanol ring-opening and follows by the Friedel-Crafts cyclization of the resulting cationic intermediate with a pendant aromatic ring. |
| ArticleNumber | 154025 |
| Author | Tsiuryn, Mikita Hurski, Alaksiej Novikau, Ilya Leushukou, Andrei |
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| Keywords | Lewis acid Cyclopropyl-allyl rearragemet Tetralines Cyclopropanols Chromanes |
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Rearrangement of cyclopropyl methanesulfonates to allylic carbocations was employed for the construction of tetralin and chromate bicyclic... |
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| SubjectTerms | Chromanes Cyclopropanols Cyclopropyl-allyl rearragemet Lewis acid Tetralines |
| Title | Construction of tetralin and chromane cores by the Lewis acid promoted ring-opening cyclization of cyclopropyl methanesulfonates |
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