Organocatalytic route to the enantioselective synthesis of syn/ anti-α-hydrazino-γ-fluoro alcohols
| Title | Organocatalytic route to the enantioselective synthesis of syn/ anti-α-hydrazino-γ-fluoro alcohols |
| Publication Type | Journal Article |
| Year of Publication | 2024 |
| Authors | Khonde, NS, Said, MS, Danve, SS, Kumar, P |
| Journal | Tetrahedron Letters |
| Volume | 145 |
| Pagination | 155179 |
| Date Published | JUL |
| Type of Article | Article |
| ISSN | 0040-4039 |
| Keywords | alpha-Amination, alpha-Fluorination, diastereoselectivity, Enantioselectivity, HWE olefination, organocatalyst |
| Abstract | A general organocatalytic method has been developed for the asymmetric synthesis of alpha-hydrazino-gamma-fluoro alcohols, a precursor to syn/anti-1,3-fluoro amines. The strategy employs alpha-fluorination catalyzed by prolinederived catalyst, (S)-alpha,alpha-bis[3,5-bis(trifluoromethyl)phenyl]-2-pyrrolidinemetha nol trimethylsilyl ether followed by Horner-Wadsworth-Emmons (HWE) olefination of aldehydes, and proline-catalyzed alpha-amination as the key steps. The title compounds showed excellent diastereoselectivity (up to 99:1) and enantioselectivity (up to 99 %). |
| DOI | 10.1016/j.tetlet.2024.155179 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 1.8 |
Divison category:
Organic Chemistry
Database:
Web of Science (WoS)