State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China.
Chem Commun (Camb). 2021 Jun 1;57(44):5390-5393. doi: 10.1039/d1cc01929e.
Herein, we report an N-alkylation of pyrroles triggered by an unprecedented selective ring-expansive migration of the spiro-2H-pyrrole intermediates obtained via Ir-catalyzed asymmetric allylic dearomatization. The reaction affords a series of tetrahydropyrrolo[1,2-c]pyrimidine derivatives in good yields (up to 88%) with excellent enantioselectivity (up to >99% ee). The proposed reaction mechanism is supported by DFT calculations and the characterization of the key intermediate.
在这里，我们报告了一种前所未有的 Ir 催化不对称烯丙基去芳构化反应中得到的螺-2H-吡咯中间体的选择性环扩张迁移引发的吡咯的 N-烷基化反应。该反应以优异的对映选择性（高达>99%ee）和良好的收率（高达 88%）得到一系列四氢吡咯并[1,2-c]嘧啶衍生物。该反应机制得到了 DFT 计算和关键中间体的表征的支持。
