Synthesis of ferrocenyl-oxazolines by ring expansion of N-ferrocenoyl-aziridine-2-carboxylic esters
Bonini, BF; Fochi, M; Comes-Franchini, M; Ricci, A; Thijs, L; Zwanenburg, B
| HERO ID | 4936078 |
|---|---|
| In Press | No |
| Year | 2003 |
| Title | Synthesis of ferrocenyl-oxazolines by ring expansion of N-ferrocenoyl-aziridine-2-carboxylic esters |
| Authors | Bonini, BF; Fochi, M; Comes-Franchini, M; Ricci, A; Thijs, L; Zwanenburg, B |
| Journal | Tetrahedron: Asymmetry |
| Volume | 14 |
| Issue | 21 |
| Page Numbers | 3321-3327 |
| Abstract | A synthesis of ferrocenyl-oxazolines is described using an iodide-mediated ring expansion of N-ferrocenoyl-aziridine-2-carboxylic esters. The ring enlargements take place with full stereocontrol, namely net retention of configuration. Modification of the ester function by a Grignard reaction leads to three new types of ferrocenyl-oxazoline carbinol ligands, which were used as chiral ligands in the asymmetric addition of diethylzinc to benzaldehyde (e.e.s ranging from 46 to 62%). The planar chiral ferrocenyl-oxazoline carbinol ligand gave a very good result (e.e. 90%) in the palladium-catalyzed allylic substitution of 1,3-diphenyl prop-2-enylacetate with dimethyl malonate. (C) 2003 Elsevier Ltd. All rights reserved. |
| Doi | 10.1016/j.tetasy.2003.08.001 |
| Wosid | WOS:000186352300011 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |