Brnsted Acid Catalyzed Propargylation of 1,3-Dicarbonyl Derivatives. Synthesis of Tetrasubstituted Furans

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• 作者：Roberto Sanz ; Delia Miguel ; Alberto Mart&iacute ; nez ; Julia M. Á ; lvarez-Gutié ; rrez ; Fé ; lix Rodr&iacute ; guez
• 刊名：Organic Letters
• 出版年：2007
• 出版时间：February 15, 2007
• 年：2007
• 卷：9
• 期：4
• 页码：727 - 730
• 全文大小：91K
• 年卷期：v.9,no.4(February 15, 2007)
• ISSN：1523-7052

文摘

Simple Brnsted acids such as p-toluenesulfonic acid monohydrate (PTS) efficiently catalyze a direct substitution of the hydroxyl group inpropargylic alcohols with 1,3-dicarbonyl compounds. Selective propargylation or allenylation is obtained depending on the nature of thealkynol. Reactions can be performed in air in undried solvents with water being the only side product of the process. By applying this reactionas the key step, a range of interesting polysubstituted furans can easily be synthesized in a one-pot procedure.