Abstract
The first organocatalytic asymmetric reaction of 3-isothiocyanatooxindoles with nitro olefins has been developed by using a cinchonidine-derived bifunctional catalyst. The resulting products, highly functionalized 3,2′-pyrrolidinyl-substituted spirooxindole derivatives, were obtained in high yields with good diastereo- and enantioselectivities (up to dr >20:1 and er = 96:4). This Michael addition/cyclization cascade reaction employs monosubstituted nitro olefins and complements the ZnII-catalyzed variant, which is only applicable to disubstituted nitro olefins. The first organocatalytic asymmetric reaction of 3-isothiocyanatooxindoles with nitro olefins has been developed by using a cinchonidine-derived bifunctional catalyst. The resulting products, highly functionalized 3,2′-pyrrolidinyl spirooxindole derivatives, were obtained in high yields with good diastereo- and enantioselectivities (dr up to >20:1 and er = 96:4).
| Original language | English |
|---|---|
| Pages (from-to) | 6696-6700 |
| Number of pages | 5 |
| Journal | European Journal of Organic Chemistry |
| Volume | 2014 |
| Issue number | 30 |
| DOIs | |
| Publication status | Published - 2014 Oct 1 |
| Externally published | Yes |
Keywords
- Asymmetric catalysis
- Cascade reactions
- Michael addition
- Nitrogen heterocycles
- Spiro compounds
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry