Concise enantioselective synthesis of (2S,3S)-3-hydroxypipecolic acid via proline catalyzed alpha-aminooxylation of aldehydes and Pd-catalyzed ether directed aza-Claisen rearrangements
| Title | Concise enantioselective synthesis of (2S,3S)-3-hydroxypipecolic acid via proline catalyzed alpha-aminooxylation of aldehydes and Pd-catalyzed ether directed aza-Claisen rearrangements |
| Publication Type | Journal Article |
| Year of Publication | 2015 |
| Authors | Ahuja, BBhushan, Sudalai, A |
| Journal | Tetrahedron-Asymmetry |
| Volume | 26 |
| Issue | 1 |
| Pagination | 24-28 |
| Date Published | JAN |
| Type of Article | Article |
| ISSN | 0957-4166 |
| Abstract | An efficient approach to (2S,3S)-3-hydroxypipecolic acid with an overall yield of 10.2% and 98% ee starting from 1,5-pentanediol has been developed. The key steps employed in the synthesis are the D-proline catalyzed sequential alpha-aminooxylation/Horner-Wadsworth-Emmons olefination of an aldehyde and the Pd-catalyzed MOM-ether directed aza-Claisen rearrangement of an allylic trichloroacetimidate. (C) 2014 Elsevier Ltd. All rights reserved. |
| DOI | 10.1016/j.tetasy.2014.11.010 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 2.108 |
Divison category:
Chemical Engineering & Process Development
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