聚合物支持的苯并噁嗪并[4,3-b][1,2,5]噻二嗪酮 6,6-二氧化物的立体选择性合成。
Polymer-Supported Stereoselective Synthesis of Benzoxazino[4,3-b][1,2,5]thiadiazepinone 6,6-dioxides.
机构信息
Department of Organic Chemistry, Faculty of Science, Palacký University , 771 46 Olomouc, Czech Republic.
JEOL Resonance, Inc. , Musashino 3-1-2, Akishima, Tokyo 196-8558, Japan.
出版信息
ACS Comb Sci. 2017 Oct 9;19(10):670-674. doi: 10.1021/acscombsci.7b00115. Epub 2017 Aug 31.
Herein, we report the stereoselective synthesis of trisubstituted benzoxazino[4,3-b][1,2,5]thiadiazepinone 6,6-dioxides from polymer-supported Fmoc-Ser(tBu)-OH and Fmoc-Thr(tBu)-OH. After the solid-phase synthesis of N-alkylated-N-sulfonylated intermediates using various 2-nitrobenzenesulfonyl chlorides and bromoketones, the target compounds were obtained via trifluoroacetic acid (TFA)-mediated cleavage from the resin, followed by cyclization of the diazepinone scaffold. Except for the threonine-based intermediates, the inclusion of triethylsilane (TES) in the cleavage cocktail yielded a specific configuration of the newly formed C chiral center. The final cyclization resulted in minor or no inversion of the C stereocenter configuration.
在此，我们报告了从聚合物负载的 Fmoc-Ser(tBu)-OH 和 Fmoc-Thr(tBu)-OH 立体选择性合成三取代苯并恶嗪[4,3-b][1,2,5]噻二氮杂卓 6,6-二氧化物。在使用各种 2-硝基苯磺酰氯和溴代酮进行 N-烷基化-N-磺酰化中间体的固相合成后，通过三氟乙酸（TFA）介导从树脂上裂解得到目标化合物，然后对二氮杂卓骨架进行环化。除了苏氨酸中间体外，在裂解混合物中加入三乙基硅烷（TES）可得到新形成的 C 手性中心的特定构型。最后环化反应导致 C 立体中心构型的反转较小或没有。
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