Abstract
An organocatalyzed diastereo- and enantioselective cascade aza-Michael/Michael addition of 2-tosylaminoenones to unsaturated pyrazolones has been developed to afford novel chiral spiropyrazolone tetrahydroquinolines containing three contiguous stereocenters. This cascade reaction proceeded well with 2 mol% chiral bifunctional tertiary amine squaramide catalyst to give the desired products in excellent yields (up to 99%) with excellent diastereoselectivity (up to > 25:1 diastereomeric ratio) and high enantioselectivity (up to 91% enantiomeric excess).
| Original language | English |
|---|---|
| Pages (from-to) | 3278-3286 |
| Number of pages | 9 |
| Journal | Chemistry - An Asian Journal |
| Volume | 9 |
| Issue number | 11 |
| DOIs | |
| Publication status | Published - Nov 2014 |
Keywords
- Asymmetric synthesis
- Domino reactions
- Heterocycles
- Michael addition
- Organocatalysis