Hiremath, M. and Sunil Kumar, Y. C. and Umashankara, M. and Sandhya, N. C. and Chandrappa, S. and Pavan Kumar, C. S. and Mantelingu, K. and Rangappa, K. S. (2016) Stereoselective synthesis of N-benzyl (2S,3S,4S)-3-hydroxy-4-methylproline. Tetrahedron: Asymmetry, 27 (6). 261 - 267.
Full text not available from this repository. (Request a copy)Abstract
The synthesis of (2S,3S,4S)-N-benzyl-3-hydroxy 4-methyl proline and its stereoisomer (2R,3R,4S)-N-benzyl-3-hydroxy 4-methyl proline has been achieved starting with the conjugate addition of methyl methacrolate and benzylamine. The other key reactions performed in our strategy include enzymatic separation of an α-methyl β-amino alcohol, Sharpless asymmetric dihydroxylation of an α,β-unsaturated δ-amino ester, and intramolecular cyclization of a sulfonate to a pyrrolidine ring system. Two stereoisomers were synthesized from the common α,β-unsaturated δ-amino ester intermediate. This protocol is simple, straightforward, efficient, highly stereoselective, and economically viable.
| Item Type: | Article |
|---|---|
| Subjects: | C Chemical Science > Chemistry |
| Divisions: | Department of > Chemistry |
| Depositing User: | Manjula P Library Assistant |
| Date Deposited: | 21 Jun 2019 10:36 |
| Last Modified: | 21 Jun 2019 10:36 |
| URI: | http://eprints.uni-mysore.ac.in/id/eprint/3627 |
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