Organocatalytic Asymmetric [4+2]-Cycloadditions of 2-Aminophenyl Enones with Isatin-Derived Ketimines: Diastereo- and Enantioselective Synthesis of Spirooxindole-Tetrahydroquinazolines

被引：8

作者：

Han, Ji Won ^{[1
]}

Kim, Yoseop ^{[1
]}

Kim, Sung-Gon ^{[1
]}

机构：

[1] Kyonggi Univ, Coll Nat Sci, Dept Chem, Suwon 16227, South Korea

来源：

ORGANIC LETTERS | 2023年 / 26卷 / 01期

基金：

新加坡国家研究基金会;

关键词：

1,3-DIPOLAR CYCLOADDITIONS; CONSTRUCTION; IMINES; STEREOCENTERS; DERIVATIVES; INHIBITORS; OXINDOLES; ACCESS;

D O I：

10.1021/acs.orglett.3c03918

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel method for the enantioselective synthesis of spiro N,N-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).

引用

页码：252 / 257

页数：6

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