2,5-cis-2,3,5-Trisubstituted tetrahydrofurans from the diastereomixture of 2,4-disubstituted 1,3-dioxepins via stereomutation |
| |
| Authors: | Kubo Ozora Yahata Kenzo Maegawa Tomohiro Fujioka Hiromichi |
| |
| Institution: | Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka, 565-0871, Japan. |
| |
| Abstract: | A diastereoselective ring contraction of the diastereomixture of 2,4-disubstituted 1,3-dioxepins to 2,5-cis-2,3,5-trisubstituted tetrahydrofurans was achieved using TfOH in DMF. The reaction appears to proceed via a chair-like transition state, in which stereomutation of the oxocarbenium occurred, followed by an aldol-type cyclization. |
| |
| Keywords: | |
| 本文献已被 PubMed 等数据库收录！ |
|
