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  • Title: Highly enantioselective synthesis of 5-phenyl-2-alkylprolines using phase-transfer catalytic alkylation.
    Author: Lee M, Lee YJ, Park E, Park Y, Ha MW, Hong S, Lee YJ, Kim TS, Kim MH, Park HG.
    Journal: Org Biomol Chem; 2013 Mar 28; 11(12):2039-46. PubMed ID: 23389435.
    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 α-alkylated analogues of (+)-RP66803, as potential CCK antagonists.
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