Gopi, Elumalai ; Namboothiri, Irishi N. N. (2013) Synthesis of Fused Bromofurans via Mg-Mediated Dibromocyclopropanation of Cycloalkanone-Derived Chalcones and Cloke–Wilson Rearrangement Journal of Organic Chemistry, 78 (3). pp. 910-919. ISSN 0022-3263
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Official URL: http://doi.org/10.1021/jo3022988
Related URL: http://dx.doi.org/10.1021/jo3022988
Abstract
A convenient two-step sequence for the conversion of alkylidenecycloalkanones to bromofurans is reported. The steps involve Mg-mediated diastereoselective dibromocyclopropanation of alkylidenecycloalkanone followed by acidic alumina-mediated regioselective ring expansion of the cyclopropyl ketone. The scope of the reaction was investigated using alkylidenecycloalkanones derived from tetralone, indanone, and benzosuberone to afford 2-aryl-3-bromofurans fused to various benzocycloalkanes. Representative examples of stereoconvergent dibromocyclopropanation and total aromatization of the furobenzocycloalkane are also reported.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 121550 |
| Deposited On: | 19 Jul 2021 08:32 |
| Last Modified: | 19 Jul 2021 08:32 |
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