Highly enantioselective synthesis of 5-phenyl-2-alkylprolines using phase-transfer catalytic alkylation
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Title
- Highly enantioselective synthesis of 5-phenyl-2-alkylprolines using phase-transfer catalytic alkylation
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Author(s)
- Lee, Myungmo; Lee, Young-Ju; Park, Eunyoung; Park, Yohan; Ha, Min Woo; Hong, Suckchang; Lee, Yeon-Ju; Kim, Taek-Soo; Kim, Mi-hyun; Park, Hyeung-geun
- KIOST Author(s)
- Lee, Yeon Ju(이연주)
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Alternative Author(s)
- 이연주
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Publication Year
- 2013
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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.
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ISSN
- 1477-0520
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URI
- https://sciwatch.kiost.ac.kr/handle/2020.kiost/3320
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DOI
- 10.1039/c3ob27089k
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Bibliographic Citation
- ORGANIC & BIOMOLECULAR CHEMISTRY, v.11, no.12, pp.2039 - 2046, 2013
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Publisher
- ROYAL SOC CHEMISTRY
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Subject
- 1,3-DIPOLAR CYCLOADDITION; ASYMMETRIC-SYNTHESIS; AZOMETHINE YLIDES; ANALOGS; DESIGN; SALTS; ESTER; ACIDS
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Type
- Article
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Language
- English
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Document Type
- Article
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