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给体-受体环丙烷的开环1,3-氨基硫属化反应:一种三组分方法

Ring-Opening 1,3-Aminochalcogenation of Donor-Acceptor Cyclopropanes: A Three-Component Approach.

作者信息

Augustin André U, Jones Peter G, Werz Daniel B

机构信息

Institute of Organic Chemistry, Technische Universität Braunschweig, Hagenring 30, 38106, Braunschweig, Germany.

Institute of Inorganic and Analytical Chemistry, Technische Universität Braunschweig, Hagenring 30, 38106, Braunschweig, Germany.

出版信息

Chemistry. 2019 Sep 6;25(50):11620-11624. doi: 10.1002/chem.201902160. Epub 2019 Aug 7.

Abstract

A 1,3-aminothiolation was realized by reacting 2-substituted cyclopropane 1,1-dicarboxylates with sulfonamides and N-(arylthio)succinimides. Under Sn(OTf) catalysis the transformation proceeded smoothly to the corresponding ring-opened products bearing the sulfonamide in the 1-position next to the donor and the arylthio residue in the 3-position next to the acceptor. The procedure was extended to the corresponding selenium analogues by employing N-(phenylseleno)succinimides as an electrophilic selenium source.

摘要

通过使2-取代的环丙烷-1,1-二羧酸酯与磺酰胺和N-(芳硫基)琥珀酰亚胺反应实现了1,3-氨基硫醇化反应。在三氟甲磺酸锡催化下,转化反应顺利进行,生成相应的开环产物,该产物在供体旁边的1位带有磺酰胺,在受体旁边的3位带有芳硫基残基。通过使用N-(苯基硒基)琥珀酰亚胺作为亲电硒源,该方法扩展到了相应的硒类似物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3c08/6771889/23285c4636ad/CHEM-25-11620-g001.jpg

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