Enantioselective Synthesis of Chiral α-Thio-Quaternary Stereogenic Centers via Phase-Transfer-Catalyzed α-Alkylation of α-Acylthiomalonates,The Journal of Organic Chemistry

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Enantioselective Synthesis of Chiral α-Thio-Quaternary Stereogenic Centers via Phase-Transfer-Catalyzed α-Alkylation of α-Acylthiomalonates
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2018-01-10 00:00:00 , DOI: 10.1021/acs.joc.7b02605
Min Woo Ha ₁ , Jun Young Lee ₁ , Doyoung Kim ₁ , Geumwoo Lee ₁ , Jae Kyun Lee ₂ , Suckchang Hong ₁ , Hyeung-geun Park ₁

Affiliation

An efficient synthetic method for establishing chiral α-thio-α-quaternary stereogenic center was successfully developed. The enantioselective α-alkylation of α-acylthiomalonates under phase-transfer catalytic conditions [50% aq. KOH, toluene, −20 °C, and (S,S)-3,4,5-trifluorophenyl-NAS bromide] provided the corresponding α-acylthio-α-alkylmalonates in high chemical yields (up to 99%) and high optical yields (up to 98% ee).

中文翻译：

通过相转移催化的α-酰基硫代丙二酸酯的α-烷基化手性α-硫-季位立体中心的对映选择性合成

成功开发了一种建立手性α-硫代-α-四元立体异构中心的有效合成方法。α-酰基硫代丙二酸酯在相转移催化条件下[50％aq。KOH，甲苯，-20°C和（S，S）-3,4,5-三氟苯基-NAS溴化物]以高化学产率（高达99％）和高光学产率提供了相应的α-酰基硫代-α-烷基丙二酸酯产量（高达98％ee）。

更新日期：2018-01-10

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