Desymmetrization of spiro-activated meso-cyclopropanes via nucleophilic substitution |
| |
| Authors: | Paul Mü ller,David Riegert |
| |
| Affiliation: | Department of Organic Chemistry, University of Geneva, 30, Quai Ernest Ansermet, CH-1211 Geneva 4, Switzerland |
| |
| Abstract: | The spiro-activated cyclopropane 1 undergoes desymmetrization either with Li-thiophenoxide in the presence of a chiral complexing ligand, or with ion pairs formed from thiophenols and aromatic chiral amines. The latter procedure is more efficient and provides the ring-opened thioether 6 in up to 79% yield and up to 60% ee. |
| |
| Keywords: | Nucleophilic substitution Chiral ion pairs Thiophenoxide Chiral ligand Chinchonine |
| 本文献已被 ScienceDirect 等数据库收录！ |
