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*

*Corresponding author for this work

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Abstract

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.

Original languageEnglish
Pages (from-to)7181-7185
Number of pages5
JournalOrganic and Biomolecular Chemistry
Volume19
Issue number33
DOIs
Publication statusPublished - 7 Sept 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