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

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...

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Detalles Bibliográficos
Autores principales: Hao, Yu, Li, Zi-Hao, Ma, Zhi-Gang, Liu, Ru-Xin, Ge, Rui-Tian, Li, Quan-Zhe, Ding, Tong-Mei, Zhang, Shu-Yu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10498726/
https://www.ncbi.nlm.nih.gov/pubmed/37712017
http://dx.doi.org/10.1039/d3sc02705h
Descripción
Sumario: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.