Cyclopentylglycine (Cpg) is a competitive inhibitor of isoleucine uptake in E. coli [1] and also has been used in designing angiotensin II antagonists [2]. We exploited a commercially available chiral auxillary [3] to obtain Cpg. Thus, stereoselective alkylation of the enolate derived from benzyl (2
Schedule for Poster Presentations; Abstracts of Poster Section A; Abstracts of Poster Section B
- Publisher
- Wiley (John Wiley & Sons)
- Year
- 2003
- Tongue
- English
- Weight
- 435 KB
- Volume
- 71
- Category
- Article
- ISSN
- 0006-3525
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โฆ Synopsis
We report a general approach to the synthesis of Boc-protected 4-alkylprolines via asymmetric hydrogenation reactions. Starting from trans-4-hydroxyproline, the key unsaturated intermediates were obtained by Wittig-type reactions at the 4 position. The Crabtree catalyst (Ir[COD]PyPCy 3 PF 6 ) proved to be effective in the diastereoselective reduction of exocyclic olefins to give trans-substituted pyrrolidines. Good facial selectivities were also observed in heterogeneous hydrogenations with Raney-Ni to yield cis-substituted pyrrolidines. The incorporation of substituted prolines and prolinols obtained by this strategy into biologically relevant peptidomimetics will be discussed.
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