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Asymmetric [4 + 2] cycloaddition synthesis of 4H-chromene derivatives facilitated by group-assisted-purification (GAP) chemistry

In this work, we present a strategy for the preparation of functionalized 4H-chromene derivatives via a Cs(2)CO(3)-catalyzed [4 + 2] cycloaddition of enantiopure chiral salicyl N-phosphonyl imines with allenoates. Fifteen examples were achieved in excellent yields and diastereoselectivity. The produ...

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Detalles Bibliográficos
Autores principales: Rouh, Hossein, Tang, Yao, Zhang, Sai, Ali, Ahmed I. M., Surowiec, Kazimierz, Unruh, Daniel, Li, Guigen
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9044656/
https://www.ncbi.nlm.nih.gov/pubmed/35494146
http://dx.doi.org/10.1039/d1ra08323f
Descripción
Sumario:In this work, we present a strategy for the preparation of functionalized 4H-chromene derivatives via a Cs(2)CO(3)-catalyzed [4 + 2] cycloaddition of enantiopure chiral salicyl N-phosphonyl imines with allenoates. Fifteen examples were achieved in excellent yields and diastereoselectivity. The products were purified simply by washing the crude mixture with hexanes following the Group-Assisted Purification (GAP) chemistry/technology to bypass traditional separation methods. The absolute configuration was unambiguously determined by X-ray structure analysis.