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Enantioselective approach to 3-substituted prolines
β Scribed by Theodore M Kamenecka; You-Jung Park; Linus S Lin; Thomas Lanza Jr.; William K Hagmann
- Publisher
- Elsevier Science
- Year
- 2001
- Tongue
- French
- Weight
- 53 KB
- Volume
- 42
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
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. Cleavage of the trityl residue and hydrogenation provided final products with good to modest diastereoselectivity.
π SIMILAR VOLUMES
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.