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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 
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.
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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