Han Ji Won, Kim Yoseop, Kim Sung-Gon
Department of Chemistry, College of Natural Science, Kyonggi University, 154-42, Gwanggyosan-ro, Yeongtong-gu, Suwon, 16227, Republic of Korea.
Org Lett. 2024 Jan 12;26(1):252-257. doi: 10.1021/acs.orglett.3c03918. Epub 2023 Dec 26.
A novel method for the enantioselective synthesis of spiro -heterocyclic oxindoles has been developed, employing asymmetric [4 + 2]-cycloadditions of 2-aminophenyl enones with isatin-derived ketimines. This method employs an organocatalytic approach, utilizing a bifunctional squaramide-based catalyst. It enables the precise synthesis of chiral spirooxindole-tetrahydroquinazolines with intricate structures, featuring chiral quaternary centers. This process achieves remarkable results, including high yields and exceptional levels of enantioselectivity and diastereoselectivity (up to 96% yield, 95% ee, and >20:1 dr).
已开发出一种对映选择性合成螺杂环氧化吲哚的新方法，该方法采用2-氨基苯烯酮与异吲哚酮衍生的酮亚胺进行不对称[4 + 2]环加成反应。此方法采用有机催化途径，利用双功能方酰胺基催化剂。它能够精确合成具有复杂结构且含有手性季碳中心的手性螺氧化吲哚-四氢喹唑啉。该过程取得了显著成果，包括高收率以及出色的对映选择性和非对映选择性水平（收率高达96%，对映体过量值达95%，非对映体比例>20:1）。
