Regioselective Synthesis of 3-Hydroxy-4,5-alkyl-Substituted Pyridines Using 1,3-Enynes as Alkynes Surrogates

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• 作者：Manuel Barday ; Kelvin Y. T. Ho ; Christopher T. Halsall ; Christophe Aïssa
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：April 15, 2016
• 年：2016
• 卷：18
• 期：8
• 页码：1756-1759
• 全文大小：405K
• 年卷期：0
• ISSN：1523-7052

文摘

The poor regioselectivity of the [4 + 2] cycloaddition of 3-azetidinones with internal alkynes bearing two alkyl substituents via nickel-catalyzed carbon–carbon activation is addressed using 1,3-enynes as substrates. The judicious choice of substitution on the enyne enables complementary access to each regioisomer of 3-hydroxy-4,5-alkyl-substituted pyridines, which are important building blocks in medicinal chemistry endeavors.