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

ABSTRACT: Catalytic asymmetric dearomative [3+2] cycloaddition of α-imino γ-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.

SUBMITTER: Chen Y

PROVIDER: S-EPMC10057014 | biostudies-literature | 2023 Mar

REPOSITORIES: biostudies-literature

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

Chen Yan Y Zhao Jian-Qiang JQ Zhang Yan-Ping YP Zhou Ming-Qiang MQ Zhang Xiao-Mei XM Yuan Wei-Cheng WC

Molecules (Basel, Switzerland) 20230319 6

Catalytic asymmetric dearomative [3+2] cycloaddition of <i>α</i>-imino <i>γ</i>-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 ...[more]

PMID: 36985737

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