A Convenient Entry to 5-(sp²)-Substituted and 5,5-Disubstituted Tetronic Acids

David Tejedor, Alicia Santos-Expósito, Fernando García-Tellado*

*Instituto de Productos Naturales y Agrobiología, CSIC, Avda. Astrofísico Francisco Sánchez 3, 38206 La Laguna, Tenerife, Canary Islands, Spain, Email: fgarciaipna.csic.es

D. Tejedor, A. Santos-Expósito, F. García-Tellado, Synlett, 2006, 1607-1609.

DOI: 10.1055/s-2006-941596

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Abstract

A one-pot, convenient and general access to 5-sp²-substituted and 5,5-disubstituted tetronic acids embodies two consecutive chemical events: a Michael addition of pyrrolidine on a secondary or tertiary γ-hydroxy-α,β-alkynyl ester derivative to give the corresponding enamine, and a subsequent acid-catalyzed hydrolysis-lactonization.

see article for more examples

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Key Words

alkynes, lactones, butenolides, aminations, cyclizations, Michael additions

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ID: J60-Y2006-4490