Abstract
The Reformatsky reactions of 3-2-bromopropionyl)-2-oxazolidone derivatives with various aldehydes were investigated to elucidate the effects of substituents in the 2-oxazolidone moieties on their diastereoselectivities. The highest 2,3-syn-diastereoselectivity (2,3-syn:2,3- anti=98:2) could be realized at -78°C by employing sterically crowded 3-(2- bromopropionyl)-4,4-dibutyl-5,5-pentamethylene-2-oxazolidone. While high 2,3-syn-3,4-syn-selectivity (2,3-syn-3,4-syn:2,3-syn-3,4-anti=94:6) was also accomplished by the reaction with di-2-phenylpropanal, application of this reaction to enantioselective synthesis of 2,3-syn-aldols was found to be unrewarding. The observed diastereoselectivities could be accounted for by the chelating transition state models.
| Original language | English |
|---|---|
| Pages (from-to) | 2821-2834 |
| Number of pages | 14 |
| Journal | Tetrahedron |
| Volume | 47 |
| Issue number | 16-17 |
| DOIs | |
| Publication status | Published - 1991 |
| Externally published | Yes |
All Science Journal Classification (ASJC) codes
- Biochemistry
- Drug Discovery
- Organic Chemistry