Squaramide-catalysed asymmetric Michael addition/cyclization cascade reaction of 4-arylmethylidene-2,3-dioxopyrrolidines with 2-isothiocyanato-1-indanones

Xi Qiang Hou, Jiang Bo Wen, Li Yan, Da Ming Du*

*此作品的通讯作者

科研成果: 期刊稿件文章同行评审

9 引用 (Scopus)

摘要

A highly efficient cinchona alkaloid-derived squaramide catalysed asymmetric Michael/cyclization cascade reaction of 4-arylmethylidene-2,3-dioxopyrrolidines with 2-isothiocyanato-1-indanones was successfully developed. This protocol provides an efficient and mild access to indanone-derived spiropyrrolidone scaffolds containing three contiguous stereocenters with two spiroquaternary stereocenters in excellent yields (up to 99%) with high enantio- and diastereoselectivities (up to 99% ee and up to >20 : 1 dr). This method provides an economical and practical approach for the asymmetric synthesis of medicinally relevant molecules.

源语言英语
页(从-至)7181-7185
页数5
期刊Organic and Biomolecular Chemistry
19
33
DOI
出版状态已出版 - 7 9月 2021

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Hou, X. Q., Wen, J. B., Yan, L., & Du, D. M. (2021). Squaramide-catalysed asymmetric Michael addition/cyclization cascade reaction of 4-arylmethylidene-2,3-dioxopyrrolidines with 2-isothiocyanato-1-indanones. Organic and Biomolecular Chemistry, 19(33), 7181-7185. https://doi.org/10.1039/d1ob01223a