Phosphine-Catalyzed Asymmetric (3 + 2) Annulations of δ-Acetoxy Allenoates with β-Carbonyl Amides: Enantioselective Synthesis of Spirocyclic β-Keto γ-Lactams.
Phosphine-Catalyzed Asymmetric (3 + 2) Annulations of δ-Acetoxy Allenoates with β-Carbonyl Amides: Enantioselective Synthesis of Spirocyclic β-Keto γ-Lactams.
复制标题
DOI：
10.1021/acs.orglett.7b01717
复制
发表时间：
2017-06
期刊：
影响因子：
5.2
通讯作者：
Chunjie Ni;Jiangfei Chen;Yuwen Zhang;Yading Hou;Dong Wang;Xiaofeng Tong;Shou‐Fei Zhu;Qi‐Lin Zhou
中科院分区：
文献类型：
--
作者：
Chunjie Ni;Jiangfei Chen;Yuwen Zhang;Yading Hou;Dong Wang;Xiaofeng Tong;Shou‐Fei Zhu;Qi‐Lin Zhou
虽然膦催化是构建N-杂环的有力工具，但膦催化的内酰胺环化反应仍然非常罕见。本文报道了在（R）-SITCP催化下δ-乙酰氧基丙二烯酸酯与β-羰基酰胺的不对称（3 + 2）成环反应。联烯酸的δC和γC分别与酰胺的αC和N进行环化，形成具有良好至优异立体选择性的γ-内酰胺。
While the phosphine catalysis is a powerful tool for the construction of N-heterocycles, the phosphine-catalyzed annulations toward lactam motif are still extremely scarce. Here, we report the asymmetric (3 + 2) annulations of δ-acetoxy allenoates with β-carbonyl amides by using the (R)-SITCP catalyst. The δC and γC of allenoate respectively engage in annulation with the αC and N of the amide, forging a γ-lactam with good to excellent stereoselectivity.