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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Bibliographic Details
Published in:	Tetrahedron letters Vol. 104; p. 154025
Main Authors:	Novikau, Ilya, Leushukou, Andrei, Tsiuryn, Mikita, Hurski, Alaksiej
Format:	Journal Article
Language:	English
Published:	Elsevier Ltd 17-08-2022
Subjects:	Chromanes Cyclopropanols Cyclopropyl-allyl rearragemet Lewis acid Tetralines Lewis acid Cyclopropyl-allyl rearragemet Tetralines Cyclopropanols Chromanes
Online Access:	Get full text
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Summary:	[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.
ISSN:	0040-4039 1873-3581
DOI:	10.1016/j.tetlet.2022.154025