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Highly enantioselective synthesis of 5-phenyl-2-alkylprolines using phase-transfer catalytic alkylation
Cited 18 time in
Web of Science
Cited 18 time in Scopus
- Authors
- Issue Date
- 2013-03
- Publisher
- Royal Society of Chemistry
- Citation
- Organic and Biomolecular Chemistry, Vol.11 No.12, pp.2039-2046
- Abstract
- An efficient enantioselective synthetic method for the synthesis of (2R)-5-phenyl-2-alkylproline tert-butyl esters was reported. The phase-transfer catalytic alkylation of tert-butyl-5-phenyl-3,4-dihydro-2H-pyrrole-2-carboxylate in the presence of chiral quaternary ammonium catalysts gave the corresponding alkylated products (up to 97% ee). The following diastereoselective reductions afforded chiral 5-phenyl-2-alkylprolines which can be applied to asymmetric synthesis as organocatalysts or synthesis of biologically active proline based compounds, such as chiral a-alkylated analogues of (+)-RP66803, as potential CCK antagonists.
- ISSN
- 1477-0520
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