A practical synthesis of enantiopure <i>syn</i> -β-amino-α-hydroxy acids from α-amino acids with application in the formal syntheses of <scp>l</scp> -TFB-TBOA and (S)-vigabatrin
Enantiopure <i>syn</i>-β-amino-α-hydroxy acids have been synthesized from α-amino acids in a multi-step procedure that exhibits a high level of stereoselectivity and good overall yields. A stepwise oxidation of the terminal olefin to a carboxylic acid delivered an essentially quantitative yield <i>via</i> a cleaner process relative to the conventional one-pot oxidation. The practical value of this transformation has been demonstrated in the formal synthesis of l-TFB-TBOA and (S)-vigabatrin.
Authors
- X Chen
- Xiaozhong Peng (ORCID: https://orcid.org/0000-0002-9592-9554)
- Mengmeng Jiang (ORCID: https://orcid.org/0000-0002-9069-0150)
- Zhengzhi Wu
- Bohua Long (ORCID: https://orcid.org/0000-0002-8558-8987)
- Pengfei Guo (ORCID: https://orcid.org/0009-0009-1989-2508)
- S Shang
Institutions
- Shenzhen Institute of Information Technology (CN)
- China-Japan Friendship Hospital (CN)
- Shenzhen Second People's Hospital (CN)
Publication Details
- Journal
- RSC Advances
- Published
- 2025-01-01
- DOI
- https://doi.org/10.1039/d5ra05586e
- Primary Topic
- Chemical synthesis and alkaloids
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Natural Science Foundation of Shenzhen City