Synthesis 2014; 46(09): 1197-1204
DOI: 10.1055/s-0033-1340865
paper
© Georg Thieme Verlag Stuttgart · New York

Base-Promoted One-Pot Sequential Phosphite Addition and 5-exo-dig Cyclization of Enynals: A Facile Route to Trisubstituted Furans

Anasuyamma Uravakilli
School of Chemistry, University of Hyderabad, Hyderabad 500 046, A. P., India   Email: kckssc@uohyd.ac.in   Email: kckssc@yahoo.com   Fax: +91(40)23012460
,
Ramesh Kotikalapudi
School of Chemistry, University of Hyderabad, Hyderabad 500 046, A. P., India   Email: kckssc@uohyd.ac.in   Email: kckssc@yahoo.com   Fax: +91(40)23012460
,
K. C. Kumara Swamy*
School of Chemistry, University of Hyderabad, Hyderabad 500 046, A. P., India   Email: kckssc@uohyd.ac.in   Email: kckssc@yahoo.com   Fax: +91(40)23012460
› Author Affiliations
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.

Supporting Information