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Axially chiral styrene-based organocatalysts and their application in asymmetric cascade Michael/cyclization reaction.

ABSTRACT: An axially chiral styrene-based organocatalyst, featuring a combination of axially chiral styrene-based structure and a pyrrole ring, has been designed and synthesized. This catalyst demonstrates remarkable capabilities in producing a wide range of densely substituted spirooxindoles that feature an alkyne-substituted quaternary stereogenic center. These spirooxindoles are generated through mild cascade Michael/cyclization reactions, resulting in high conversion rates and exceptional enantioselectivity. Our catalytic model, based on experiments, X-ray structure analysis and DFT calculations suggests that chiral matched π-π interactions and multiple H-bonds between the organocatalyst and substrates play significant roles in controlling the stereoselectivity of the reaction.

SUBMITTER: Hao Y

PROVIDER: S-EPMC10498726 | biostudies-literature | 2023 Sep

REPOSITORIES: biostudies-literature

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Axially chiral styrene-based organocatalysts and their application in asymmetric cascade Michael/cyclization reaction.

Hao Yu Y Li Zi-Hao ZH Ma Zhi-Gang ZG Liu Ru-Xin RX Ge Rui-Tian RT Li Quan-Zhe QZ Ding Tong-Mei TM Zhang Shu-Yu SY

Chemical science 20230816 35

An axially chiral styrene-based organocatalyst, featuring a combination of axially chiral styrene-based structure and a pyrrole ring, has been designed and synthesized. This catalyst demonstrates remarkable capabilities in producing a wide range of densely substituted spirooxindoles that feature an alkyne-substituted quaternary stereogenic center. These spirooxindoles are generated through mild cascade Michael/cyclization reactions, resulting in high conversion rates and exceptional enantioselec ...[more]

PMID: 37712017

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