Simultaneous Construction of C–N Axial and Central Chirality via Silver-Catalyzed Desymmetrizative [3 + 2] Cycloaddition of Prochiral N-Aryl Maleimides with Activated Isocyanides,Organic Letters

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Simultaneous Construction of C–N Axial and Central Chirality via Silver-Catalyzed Desymmetrizative [3 + 2] Cycloaddition of Prochiral N-Aryl Maleimides with Activated Isocyanides
Organic Letters ( IF 4.9 ) Pub Date : 2022-06-20 , DOI: 10.1021/acs.orglett.2c01761
Sen Zhang ₁ , Zhang-Hong Luo ₁ , Wen-Tao Wang ₁ , Linghui Qian ₁ , Jia-Yu Liao _{1,

2}

Affiliation

Herein, we report an unprecedented strategy for the simultaneous construction of a remote C–N stereogenic axis and three contiguous stereogenic carbon centers via silver-catalyzed desymmetrizative [3 + 2] cycloaddition of prochiral N-aryl maleimides with activated isocyanides. This method features operational simplicity, wide substrate scope, high efficiency, and good to excellent stereoselectivity. Notably, it represents the first example of catalytic enantioselective synthesis of C–N atropisomers with the use of activated isocyanides.

中文翻译：

通过银催化前手性 N-芳基马来酰亚胺与活化异氰化物的去对称 [3 + 2] 环加成同时构建 C-N 轴和中心手性

在这里，我们报告了一种前所未有的策略，通过银催化的前手性N-芳基马来酰亚胺与活化的异氰化物的去对称 [3 + 2] 环加成同时构建远程 C-N 立体轴和三个连续的立体碳中心。该方法操作简单、底物范围广、效率高、立体选择性好。值得注意的是，它代表了第一个使用活化异氰化物催化对映选择性合成 C-N 阻转异构体的例子。

更新日期：2022-06-20

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