Organocatalytic Enantioselective alpha-Amination by Conjugate Addition of 5H-Thiazol-4-ones to Arylazocarboxylates: Access to ChiralN,S-acetals
Organocatalytic Enantioselective alpha-Amination by Conjugate Addition of 5H-Thiazol-4-ones to Arylazocarboxylates: Access to ChiralN,S-acetals
复制标题
通过将 5H-噻唑-4-酮与芳基偶氮羧酸盐共轭加成进行有机催化对映选择性 α-氨基化：获得手性 N,S-缩醛
DOI：
10.1002/ajoc.202000355
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发表时间：
2020
影响因子：
2.7
通讯作者：
Li Wenjun
中科院分区：
文献类型：
--
作者：
Lin Xiao;Fang Fang;Lin Wei;Liu Zhantao;Chang Xiaoyong;Li Pengfei;Li Wenjun
以手性磷酸为催化剂，通过5 H-噻唑-4-酮与偶氮羧酸酯的Michael加成反应，合成了具有光学活性的N，S-缩醛骨架。1-萘偶氮羧酸酯和苯基偶氮羧酸酯都是相容的，以通常高产率和对映选择性提供一系列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N，S-缩醛。
A chiral phosphoric acid catalyzed stereoselective Michael addition of 5H‐thiazol‐4‐ones to arylazocarboxylates was developed for the construction of optically activeN,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 ofN,S‐acetals featuring thiazol‐4‐one skeleton.