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Thiourea-catalyzed asymmetric domino Michael-cyclization reaction of 3-isothiocyanato oxindoles with β,γ-unsaturated α-keto esters for the synthesis of spirocyclic oxindoles.
- Source :
-
Tetrahedron . Apr2019, Vol. 75 Issue 14, p2155-2161. 7p. - Publication Year :
- 2019
-
Abstract
- Abstract A reaction between 3-isothiocyanato oxindoles and β , γ -unsaturated α -keto esters catalyzed by a chiral thiourea organocatalyst via a domino Michael-cyclization process is described, which delivers a range of biologically important 2′-thioxospiro[indoline-3,4′-oxazolidin]-2-one compounds in high yields with good diastereo- and enantioselectivities (up to 99% yield, >99:1 dr, >99% ee). Moreover, two of 2′-thioxospiro[indoline-3,4′-oxazolidin]-2-one compounds were found to significantly behave in anti-inflammatory activities in a preliminary biological evaluation. Graphical abstract Image 1 [ABSTRACT FROM AUTHOR]
- Subjects :
- *OXINDOLES
*ESTERS
Subjects
Details
- Language :
- English
- ISSN :
- 00404020
- Volume :
- 75
- Issue :
- 14
- Database :
- Academic Search Index
- Journal :
- Tetrahedron
- Publication Type :
- Academic Journal
- Accession number :
- 135349639
- Full Text :
- https://doi.org/10.1016/j.tet.2019.02.036