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Organocatalytic Enantioselective α‐Amination by Conjugate Addition of 5H‐Thiazol‐4‐ones to Arylazocarboxylates: Access to Chiral N,S‐acetals
Asian Journal of Organic Chemistry ( IF 2.7 ) Pub Date : 2020-07-08 , DOI: 10.1002/ajoc.202000355
Xiao Lin 1 , Fang Fang 2 , Wei Lin 1 , Zhantao Liu 1 , Xiaoyong Chang 2 , Pengfei Li 2, 3 , Wenjun Li 1
Affiliation  

A chiral phosphoric acid catalyzed stereoselective Michael addition of 5H‐thiazol‐4‐ones to arylazocarboxylates was developed for the construction of optically active N ,S‐acetal frameworks. Both 1‐naphthylazocarboxylates and phenylazocarboxylates were compatible to afford a series of 1,4‐adducts in generally high yields and enantioselectivities. Notably, the catalytic protocol enables the formation of N ,S‐acetals featuring thiazol‐4‐one skeleton.

中文翻译:

通过将5H-噻唑-4-酮偶合到芳基偶氮羧酸酯上来进行有机催化对映选择性α-胺化反应:获得手性N,S-缩醛

开发了一种手性磷酸催化的5 H-噻唑-4-立体选择性迈克尔加成到芳基偶氮羧酸酯,以构建旋光的NS-缩醛骨架。1-萘基偶氮羧酸酯和苯基偶氮羧酸酯都可以以高收率和对映选择性相容地提供一系列1,4-加合物。值得注意的是,催化方案能够形成具有噻唑-4-酮骨架的NS-缩醛。
更新日期:2020-08-08
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