A catalytic highly enantioselective (99% ee) preparation of N-tert-butyloxycarbonyl-(2S,3S)-3-hydroxy-2-phenyl-piperidine and N-tert-butyloxycarbonyl-(2S)-2-phenyl-piperidin-3-one was developed using an intramolecular epoxide opening followed by ring expansion. The cis-epoxide starting material was
Stereoselective synthesis of (2S,3S)-3-hydroxy-2-phenylpiperidine from d-mannitol
โ Scribed by Mallam Venkataiah; B. Venkateswara Rao; Nitin W. Fadnavis
- Book ID
- 108284418
- Publisher
- Elsevier Science
- Year
- 2009
- Tongue
- English
- Weight
- 293 KB
- Volume
- 20
- Category
- Article
- ISSN
- 0957-4166
No coin nor oath required. For personal study only.
๐ SIMILAR VOLUMES
2S)-N-Boc-3-oxo-2-phenylpiperidine 5 and (2S,3S)-N-Boc-3-hydroxy-2-phenylpiperidine 6, known chiral building blocks for the synthesis of non-peptidic substance P antagonists, were prepared from erythro (2S)-N-benzyl 2-hydroxybenzylpyrrolidine derived from (S)-N-methoxy-N-methylpyroglutamide.
The first synthesis of (2S,3R)-3-hydroxy-3-methylproline, which is a novel amino acid of polyoxypeptin, a potent inducer of apoptosis in human pancreatic carcinoma AsPC-1, was accomplished. The key feature of the synthesis is the palladium-catalyzed intramolecular N-allylation of alkenyloxirane to t