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

Anasuyamma Uravakilli; Ramesh Kotikalapudi; K. C. Kumara Swamy

doi:10.1055/s-0033-1340865

Synthesis, Inhaltsverzeichnis

Synthesis 2014; 46(09): 1197-1204
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

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

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Abstract

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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.

Key words

nucleophilic addition - enynals - cyclization - isomerization - furans - phosphorus

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Referenzen

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