Enantioselective synthesis of (R)- and (S)-alpha-alkylcysteines via phase-transfer catalytic alkylation |
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Authors: | Kim Taek-Soo Lee Yeon-Ju Jeong Byeong-Seon Park Hyeung-geun Jew Sang-sup |
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Institution: | Research Institute of Pharmaceutical Science and College of Pharmacy, Seoul National University, Seoul 151-742, Korea. |
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Abstract: | We reported efficient enantioselective synthetic methodologies for (R)-alpha-alkylcysteines and (S)-alpha-alkylcysteines. The phase-transfer catalytic alkylation of 2-phenyl-2-thiazoline-4-carboxylic acid tert-butyl ester and 2-o-biphenyl-2-thiazoline-4-carboxylic acid tert-butyl ester, in the presence of chiral catalysts (1 or 2), gave the corresponding alkylated products, which could be hydrolyzed to provide (R)-alpha-alkylcysteines (67->99% ee) and (S)-alpha-alkylcysteines (66-88% ee), respectively. |
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