Rh(II)-Catalyzed Monocyclopropanation of Pyrroles and Its Application to the Synthesis Pharmaceutically Relevant Compounds
Rh(II)-Catalyzed Monocyclopropanation of Pyrroles and Its Application to the Synthesis Pharmaceutically Relevant Compounds
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DOI：
10.1021/acs.orglett.9b02250
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发表时间：
2019-08-02
期刊：
影响因子：
5.2
通讯作者：
Davies, Huw M. L.
中科院分区：
文献类型：
--
作者：
Fu, Jiantao;Wurzer, Nikolai;Davies, Huw M. L.
在这里，我们报告了在芳基重氮乙酸盐存在下Rh（II）催化的吡咯单环丙烷化反应，提供了具有高水平对映选择性（高达> 99%ee）的相应脱芳构化产物。在Rh-2（R-p-PhTPCP）（4）的催化下，许多吡咯底物和芳基重氮乙酸酯都是相容的。利用这些有价值的手性构建块，我们进一步证明了这种转化的应用，通过合成一个homo-beta-脯氨酸类似物和β-氨基羧酸（β-ACC）衍生物的monoclopropanated产品。
Here we report Rh(II)-catalyzed monocyclopropanation reactions on pyrroles in the presence of aryldiazoacetates, providing the corresponding dearomatized products with high levels of enantioselectivity (up to >99% ee). Under the catalysis of Rh-2(R-p-PhTPCP)(4), a broad range of pyrrole substrates and aryldiazoacetates are shown to be compatible. Utilizing these valuable chiral building blocks, we further demonstrate the application of this transformation by synthesizing a homo-beta-proline analog and a beta-aminocarboxylic acid (beta-ACC) derivative from the monocyclopropanated product.