Organocatalytic asymmetric addition of thioglycolates to o-quinone methides: a route to 5-substituted-5H-benzoxathiepine-2(3H)-ones.,Organic & Biomolecular Chemistry

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Organocatalytic asymmetric addition of thioglycolates to o-quinone methides: a route to 5-substituted-5H-benzoxathiepine-2(3H)-ones.
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2020-04-15 , DOI: 10.1039/d0ob00568a
Chandan Gharui ₁ , Satya Prakash ₂ , Deepak Chopra ₂ , Subhas Chandra Pan ₁

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Herein we have developed the first enantioselective synthesis of 5-substituted-5H-benzoxathiepine-2(3H)-ones. 2-Sulfonylmethyl phenols and thioglycolates were employed as reaction partners in this method. The desired thia Michael products were obtained via bifunctional squaramide catalyzed conjugate addition reaction to in situ generated o-quinone methides and then basic hydrolysis followed by cyclization led to the formation of 5-substituted-5H-benzoxathiepine-2(3H)-ones. Broad scope and moderate to high enantioselectivities were observed for both products.

中文翻译：

硫代乙醇酸酯的有机催化不对称加成至邻醌甲基化物：通往5取代的5H-苯并噻吩-2（3H）-的途径。

在本文中，我们开发了5-取代的-5H-苯并噻吩-2-2（3H）-的第一个对映选择性合成。在该方法中，使用2-磺酰基甲基苯酚和巯基乙酸盐作为反应伙伴。通过双官能方酰胺催化的共轭加成反应，原位生成邻醌甲基化物，然后进行碱性水解，然后环化，导致形成5-取代的-5H-苯并噻吩-2（3H）-一，得到所需的迈克尔产物。两种产品均观察到宽范围和中等至高对映选择性。

更新日期：2020-04-24

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