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Synthesis 2014; 46(09): 1197-1204
DOI: 10.1055/s-0033-1340865
DOI: 10.1055/s-0033-1340865
paper
Base-Promoted One-Pot Sequential Phosphite Addition and 5-exo-dig Cyclization of Enynals: A Facile Route to Trisubstituted Furans
Further Information
Publication History
Received: 08 November 2013
Accepted after revision: 05 February 2014
Publication Date:
27 February 2014 (online)
Abstract
An easy route for the synthesis of trisubstituted furans has been demonstrated. One-pot sequential phosphite (H-phosphonate) addition to alkynylaldehydes (enynals) promoted by tripotassium phosphate leads to trisubstituted furans (phosphono-furans) via 5-exo-dig cyclization of the phosphono-alkynol intermediates. In contrast, in the presence of silver(I) tetrafluoroborate, the reaction using the same substrates leads to a diene product.
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- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
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