Tandem nucleophilic addition–cycloaddition of arynes with α-iminoesters: two concurrent pathways to imidazolidines†,Chemical Communications

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Tandem nucleophilic addition–cycloaddition of arynes with α-iminoesters: two concurrent pathways to imidazolidines†
Chemical Communications ( IF 4.3 ) Pub Date : 2018-05-31 00:00:00 , DOI: 10.1039/c8cc03806f
Hao Jia _{1,

2,

3,

4} , Zhenyan Guo _{1,

2,

3,

4} , Honglei Liu _{1,

2,

3,

4} , Biming Mao _{1,

2,

3,

4} , Xueyan Shi _{2,

3,

4,

5} , Hongchao Guo _{1,

2,

3,

4}

Affiliation

The tandem nucleophilic addition–cycloaddition reaction has been developed for the synthesis of functionalized imidazolidine derivatives. A variety of α-iminoesters and aryne precursors were well tolerated under the mild reaction conditions. This asymmetric cycloaddition afforded imidazolidine derivatives with high yields, complete regioselectivities, and excellent diastereo- and enantioselectivities. Aryne-induced ylides working as 1,3-dipoles for asymmetric cycloaddition are the notable feature of the present reaction. In the tandem reaction, the [3+2] cycloaddition of aryne-induced ylides with metallized α-iminoesters and metal-catalyzed [3+2] cycloaddition of azomethine ylide with α-iminoesters are two concurrent pathways to imidazolidines.

中文翻译：

串联亲核加成反应-亚芳基与α-亚氨基酯的环加成反应：咪唑烷的两种同时发生途径†

已经开发了串联亲核加成-环加成反应来合成功能化的咪唑烷衍生物。在温和的反应条件下，各种α-亚氨基酸酯和芳烃前体的耐受性良好。这种不对称的环加成反应提供了咪唑烷衍生物，具有高收率，完全的区域选择性以及出色的非对映和对映选择性。作为不对称环加成反应的1,3-偶极子的芳炔诱导的酰化物是本反应的显着特征。在串联反应中，亚芳基诱导的酰基化物与金属化的α-亚氨基酯的[3 + 2]环加成反应和偶氮甲碱的金属催化的α-亚氨基酯的[3 + 2]的环加成反应是向咪唑烷类的两个同时存在的途径。

更新日期：2018-05-31

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