First enantioselective synthesis of (2S,3S)-3-hydroxy-L-arginine via proline catalyzed alpha-aminooxylation of aldehyde and Pd-catalyzed ether-directed aza-Claisen rearrangement
| Title | First enantioselective synthesis of (2S,3S)-3-hydroxy-L-arginine via proline catalyzed alpha-aminooxylation of aldehyde and Pd-catalyzed ether-directed aza-Claisen rearrangement |
| Publication Type | Journal Article |
| Year of Publication | 2015 |
| Authors | Ahuja, BBhushan, Sudalai, A |
| Journal | Tetrahedron-Asymmetry |
| Volume | 26 |
| Issue | 10-11 |
| Pagination | 548-552 |
| Date Published | MAY |
| ISSN | 0957-4166 |
| Abstract | A concise enantioselective synthesis of (2S,3S)-3-hydroxy-L-arginine with an overall yield of 10.9% and 98% ee, starting from commercially available 1,4-butanediol in ten linear steps has been achieved. The key chiral inducing steps are D-proline catalyzed sequential alpha-aminooxylation/Horner-Wadsworth-Emmons olefination of an aldehyde and the subsequent diastereoselective MOM-ether-directed Pd-catalyzed aza-Claisen rearrangement of allylic trichloroacetimidate. (C) 2015 Elsevier Ltd. All rights reserved. |
| DOI | 10.1016/j.tetasy.2015.03.011 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 2.108 |
Divison category:
Chemical Engineering & Process Development