Department of Chemistry , Emory University , 1515 Dickey Drive , Atlanta , Georgia 30322 , United States.
Institute of Organic Chemistry , University of Regensburg , Universitätsstraße 31 , 93053 Regensburg , Germany.
Org Lett. 2019 Aug 2;21(15):6102-6106. doi: 10.1021/acs.orglett.9b02250. Epub 2019 Jul 22.
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(-PhTPCP), 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-β-proline analog and a β-aminocarboxylic acid (β-ACC) derivative from the monocyclopropanated product.
在这里，我们报告了在芳基重氮乙酸酯存在下，Rh(II)催化吡咯的单环丙烷化反应，提供了相应的去芳构化产物，具有高水平的对映选择性（高达>99%ee）。在 Rh(-PhTPCP)的催化下，广泛的吡咯底物和芳基重氮乙酸酯都具有兼容性。利用这些有价值的手性构建块，我们进一步通过从单环丙烷化产物合成同型β-脯氨酸类似物和β-氨基羧酸（β-ACC）衍生物展示了这种转化的应用。
