Formal asymmetric synthesis of (2S,4R)-4-hydroxypipecolic acid via Co(III)(salen)-catalyzed two stereocentered HKR of racemic azido epoxide
| Title | Formal asymmetric synthesis of (2S,4R)-4-hydroxypipecolic acid via Co(III)(salen)-catalyzed two stereocentered HKR of racemic azido epoxide |
| Publication Type | Journal Article |
| Year of Publication | 2015 |
| Authors | Kamble, RB, Gadre, SHaribhau, Suryavanshi, GM |
| Journal | Tetrahedron Letters |
| Volume | 56 |
| Issue | 10 |
| Pagination | 1263-1265 |
| Date Published | MAR |
| ISSN | 0040-4039 |
| Keywords | Azido epoxide, Hydrolytic kinetic resolution, lodocyclization, Piperidine |
| Abstract | An efficient formal synthesis of (2S,4R)-4-hydroxypipecolic acid has been achieved in high optical purity (99% ee) from readily available benzaldehyde. The strategy employs an iodine-induced intramolecular cyclization of a carbonate and Co-catalyzed Hydrolytic Kinetic Resolution (HKR) of two stereocentered racemic azido epoxide as the key reactions to construct chiral 1,3-amino alcohol functionality. (C) 2015 Elsevier Ltd. All rights reserved. |
| DOI | 10.1016/j.tetlet.2015.01.113 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 2.347 |
Divison category:
Chemical Engineering & Process Development