Proline catalyzed enantioselective synthesis of (2S,3S)-3-hydroxypipecolic acid and formal synthesis of (+)-swainsonine
| Title | Proline catalyzed enantioselective synthesis of (2S,3S)-3-hydroxypipecolic acid and formal synthesis of (+)-swainsonine |
| Publication Type | Journal Article |
| Year of Publication | 2016 |
| Authors | Aher, RD, Sudalai, A |
| Journal | Tetrahedron Letters |
| Volume | 57 |
| Issue | 19 |
| Pagination | 2021-2024 |
| Date Published | MAY |
| Abstract | A short enantioselective synthesis of (2S,3S)-3-hydroxypipecolic acid (overall yield: 18.8%; 96% ee) and formal synthesis of (+)-swainsonine (overall yield: 13.6%; 96% ee) have been described starting from commercially available acrolein. The synthetic strategy involves a high enantioselective L-proline catalyzed sequential c-amination and diastereoselective (dr > 99:1) Barbier allylation of aldehyde in one-pot as the key reaction. (C) 2016 Elsevier Ltd. All rights reserved. |
| DOI | 10.1016/j.tetlet.2016.03.042 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 2.347 |
Divison category:
Chemical Engineering & Process Development