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- Title
Configurationally Stable (S)- and (R)-α-Methylproline-Derived Ligands for the Direct Chemical Resolution of Free Unprotected β³-Amino Acids.
- Authors
Zhou, Shengbin; Wang, Shuni; Wang, Jiang; Nian, Yong; Peng, Panfeng; Soloshonok, Vadim A.; Liu, Hong
- Abstract
Reported herein is a chemical method for the direct resolution of unprotected racemic β-substituted-β-amino acids (β³-AAs) that uses specially designed, stable, and recyclable α- methylproline-derived chiral ligands. The versatility of this methodology is unmatched by biocatalytic approaches. The method shows a broad synthetic generality for various aryl- or alkyl-substituted β³-AAs, and the new nonracemizable ligands can be accessed readily. Furthermore, the presented method produces an excellent stereochemical outcome and has a fully recyclable source of chirality, and the reaction conditions are operationally simple and convenient. The procedure has also been successfully applied to the scalable synthesis of the anti- HIV drug maraviroc.
- Subjects
PROLINE; LIGANDS (Chemistry); RESOLUTION (Chemistry); AMINO acids; TARTARIC acid; STEREOCHEMISTRY
- Publication
European Journal of Organic Chemistry, 2018, Vol 2018, Issue 15, p1821
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201800120