Copper-Catalyzed Asymmetric Dearomative [3+2] Cycloaddition of Nitroheteroarenes with Azomethines

Catalytic asymmetric dearomative [3+2] cycloaddition of -imino -lactones with either 3-nitroindoles or 2-nitrobenzofurans by using a chiral copper complex as the catalyst was developed. A wide range of structurally diverse polyheterocyclic compounds containing spirocyclic-fused butyrolactone-pyrroli...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2023-03, Vol.28 (6), p.2765
Main Authors: Chen, Yan, Zhao, Jian-Qiang, Zhang, Yan-Ping, Zhou, Ming-Qiang, Zhang, Xiao-Mei, Yuan, Wei-Cheng
Format: Article
Language:English
Subjects:
2-nitrobenzofurans
3-nitroindoles
Alkaloids
asymmetric catalysis
Asymmetry
azomethine ylides
Butyrolactone
Catalysts
Copper
Copper compounds
Cycloaddition
dearomatization
Functional groups
Lactones
Ligands
Organic compounds
Pyrrolidine
R&D
Research & development
Schiff bases
Synthesis
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Summary:Catalytic asymmetric dearomative [3+2] cycloaddition of -imino -lactones with either 3-nitroindoles or 2-nitrobenzofurans by using a chiral copper complex as the catalyst was developed. A wide range of structurally diverse polyheterocyclic compounds containing spirocyclic-fused butyrolactone-pyrrolidine-indoline and butyrolactone-pyrrolidine-dihydrobenzofuran skeletons could be smoothly obtained with excellent results (>99:1 dr and 98% ee). The potential synthetic applications of this methodology were also demonstrated by the scale-up experiment and by the diverse transformations of one product. This method is characterized by high asymmetric induction, wide functional group tolerance and scalability, and attractive product diversification.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules28062765