Chiral NHC-Catalyzed [4+2] Cycloadditions: Highly Diastereo/Enantioselective Access to Spiro[cyclohex-4-ene-1,3' -indoles] and DFT Calculations

被引：2
|
作者：
Chen, Xiaoyu [1 ]
Xia, Siqi [1 ]
Hu, Xiaoru [1 ]
Zhong, Guofu [1 ,2 ]
Yang, Limin [1 ]
机构：
[1] Hangzhou Normal Univ, Coll Mat Chem & Chem Engn, Hangzhou 311121, Zhejiang, Peoples R China
[2] Eastern Inst Adv Study, Dept Chem, Ningbo 315200, Zhejiang, Peoples R China
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2023年 / 29卷 / 23期
基金：
中国国家自然科学基金;
关键词：
4+2] cycloaddition; DFT calculations; NHC-catalyzed; spiro[cyclohex-4-ene-1; 3 ' -indole; N-HETEROCYCLIC CARBENE; ALPHA; BETA-UNSATURATED ACYL CHLORIDES; ENANTIOSELECTIVE SYNTHESIS; BRONSTED ACID; CYCLIZATION; 3-ALKYLENYLOXINDOLES; CONSTRUCTION; ANNULATION; ESTERS; ACTIVATION;
D O I：
10.1002/chem.202203818
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A highly efficient NHC-catalyzed cycloaddition of (E)-alkenylisatins and gamma-chloroenals with a broad substrate scope has been developed to provide spiro[cyclohex-4-ene-1,3 ' -indole] in good yields (up to 99% yield) with excellent diastereo-and enantioselectivities (up to > 20:1 d.r., > 99% ee) under mild conditions without the use of metal and additives. Based on computational investigations, the role of the NHC on the diastereo-and enantioselectivity is discussed.
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收藏
页数：6
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