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https://hdl.handle.net/10316/110169| Title: | Microwave-assisted reactions of allenic esters: [3+2] annulations and allenoate-Claisen rearrangement | Authors: | Lopes, Susana M. M. Santos, Bruna S. Palacios, Francisco Melo, Teresa M. V. D. Pinho e |
Keywords: | Microwave-assisted reactions, [3+2] anellation; allenoate-Claisen rearrangement; 3-pyrrolines; cyclopentenes; hepta-2,6-dienoates | Issue Date: | 2009 | Publisher: | Arkat USA | Project: | PTDC/QUI/64470/2006 SFRH/BD/45128/2008 |
Serial title, monograph or event: | Arkivoc | Volume: | 2010 | Issue: | 5 | Abstract: | The reactivity of allenic esters towards an activated N-sulfonylimine and electron-deficient alkenes with a phosphine under microwave irradiation is explored. The methodology is shown to be efficient for the one-step synthesis of 3-pyrrolines and cyclopentenes in a regio- and diastereoselective manner. This formal [3+2] cycloaddition is complete within five minutes. It was also demonstrated that microwave irradiation is the best energy source to carry out the Lewis acid catalyzed allenoate-Claisen rearrangement leading to 3-(pyrrolidin-1-yl)hepta-2,6-dienoates. | URI: | https://hdl.handle.net/10316/110169 | ISSN: | 1551-7012 | DOI: | 10.3998/ark.5550190.0011.508 | Rights: | openAccess |
| Appears in Collections: | FCTUC Química - Artigos em Revistas Internacionais |
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| Microwave-assisted reactions of allenic esters [3+2] anellations and allenoate-Claisen rearrangement.pdf | 432.09 kB | Adobe PDF | View/Open |
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