Abstract
The stereoselectivity of the intramolecular Diels-Alder reactions of 1 and its derivatives were investigated by ab initio calculations. The stereoselectivity mainly originates from the steric repulsion and the orbital interactions. The additional s-cis and s-trans conformations by introducing the carbonyl group at the neighbor of diene or dienophile may change the stereoselectivity, hence this kind of substitution can be utilized for stereoselectivive asymmetric synthesis.
| Original language | English |
|---|---|
| Pages (from-to) | 2527-2530 |
| Number of pages | 4 |
| Journal | Bulletin of the Korean Chemical Society |
| Volume | 31 |
| Issue number | 9 |
| DOIs | |
| State | Published - 20 Sep 2010 |
Keywords
- DFT
- Intramolecular Diels-Alder reaction
- Orbital interaction
- Selectivity
- Steric repulsion