Enantioselective Synthesis of (R)- and (S)--Alkylcysteines via Phase-Transfer Catalytic Alkylation

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• 作者：Taek-Soo Kim ; Yeon-Ju Lee ; Byeong-Seon Jeong ; Hyeung-geun Park ; Sang-sup Jew
• 刊名：Journal of Organic Chemistry
• 出版年：2006
• 出版时间：October 13, 2006
• 年：2006
• 卷：71
• 期：21
• 页码：8276 - 8278
• 全文大小：90K
• 年卷期：v.71,no.21(October 13, 2006)
• ISSN：1520-6904

文摘

We reported efficient enantioselective synthetic methodologies for (R)--alkylcysteines and (S)--alkylcysteines. Thephase-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 ofchiral catalysts (1 or 2), gave the corresponding alkylatedproducts, which could be hydrolyzed to provide (R)--alkylcysteines (67->99% ee) and (S)--alkylcysteines (66-88% ee), respectively.