膦催化 δ-乙酰氧基烯酸酯与β-羰基酰胺的不对称（3 + 2）环加成反应：手性螺环β-酮γ-内酰胺的高对映选择性合成。
Phosphine-Catalyzed Asymmetric (3 + 2) Annulations of δ-Acetoxy Allenoates with β-Carbonyl Amides: Enantioselective Synthesis of Spirocyclic β-Keto γ-Lactams.
机构信息
Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering, Changzhou University , 1 Gehu Road, Changzhou, 213164, China.
State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University , Tianjin, 300071, China.
出版信息
Org Lett. 2017 Jul 7;19(13):3668-3671. doi: 10.1021/acs.orglett.7b01717. Epub 2017 Jun 28.
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.
尽管膦催化是构建 N-杂环化合物的有力工具，但膦催化的环合反应对于内酰胺结构仍然非常稀缺。在这里，我们报告了使用（R）-SITCP 催化剂，通过 δ-乙酰氧基丙二烯酸酯与β-羰基酰胺的不对称（3 + 2）环合反应。丙二烯酸酯的 δC 和 γC 分别与酰胺的 αC 和 N 环合，形成具有良好至优秀立体选择性的 γ-内酰胺。
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