Copper Catalyzed Regioselective and Stereospecific Aziridine Opening with Pyridyl Grignard Nucleophiles

Copper catalyzed regioselective and stereospecific coupling between aziridines and in situ generated pyridine Grignard reagents is reported. This method provides β-pyridylethylamines with diverse structures and functionalities from aziridines and iodopyridines. β-Pyridylethylamines are potential sca...

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Bibliographic Details
Published inOrganic letters Vol. 24; no. 14; pp. 2655 - 2659
Main Authors Lee, Jaehee, Ju, Xuan, Lee, Miseon, Jiang, Qi, Jang, Hwanjong, Kim, Wan Shin, Wu, Linglin, Williams, Suja, Wang, Xiao-Jun, Zeng, Xingzhong, Payne, Jenna, Han, Zhengxu S
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 15.04.2022
Subjects
Aziridines - chemistry
Catalysis
Copper - chemistry
Molecular Structure
Stereoisomerism
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Summary:Copper catalyzed regioselective and stereospecific coupling between aziridines and in situ generated pyridine Grignard reagents is reported. This method provides β-pyridylethylamines with diverse structures and functionalities from aziridines and iodopyridines. β-Pyridylethylamines are potential scaffolds for the synthesis of biologically active compounds often found in pharmaceuticals. The synthesis of challenging chiral dihydroazaindoles was also achieved through mild one-pot reaction conditions via aziridine opening followed by nucleophilic cyclization.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c00703