Rapid access to cis 3-substituted prolines
β Scribed by Nadia Pellegrini; Martine Schmitt; Jean-Jacques Bourguignon
- Publisher
- Elsevier Science
- Year
- 2003
- Tongue
- French
- Weight
- 100 KB
- Volume
- 44
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
The O-triflate of 2-cyano-3-oxopyrrolidine was obtained and used in a palladium coupling reaction. The resulting D 2 -pyrrolidine derivatives allowed diastereocontrol at C2 and C3 after catalytic hydrogenation and led to chiral 3-substituted prolines as conformationally constrained amino acids.
π SIMILAR VOLUMES
Enantioselective synthesis of 3-substituted prolines was achieved starting from commercially available 3-hydroxy-(S)-2proline. Palladium-mediated couplings were used to introduce a variety of groups at C3 using the corresponding enol triflate derived from N-trityl 3-oxo-(S)-2-proline methyl ester. C
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An intramolecular Mannich reaction, involving various achiral aldehydes together with an a-chiral amine is employed as the key step for a stereocontrolled synthesis of highly substituted piperidine systems. Accordingly, 12 new piperidines bearing four asymmetric centers were prepared in six steps fr
A short and efficient synthetic sequence to produce a wide variety of 3-arylpiperidines from three simple building blocks is described. The key step is a palladium-catalyzed arylation of cyclopentene.