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 language | English |
|---|---|
| Pages (from-to) | 7181-7185 |
| Number of pages | 5 |
| Journal | Organic and Biomolecular Chemistry |
| Volume | 19 |
| Issue number | 33 |
| DOIs | |
| Publication status | Published - 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