PPh 催化的 1C,3N-双亲核试剂（衍生自二级 β-酮酰胺）与 δ-乙酰氧基丙二烯酸的 [3 + 2] 螺环化反应：一种构建功能化螺环 N-杂环衍生物的方法。
PPh-Catalyzed [3 + 2] Spiroannulation of 1C,3N-Bisnucleophiles Derived from Secondary β-Ketoamides with δ-Acetoxy Allenoate: A Route to Functionalized Spiro N-Heterocyclic Derivatives.
机构信息
Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology , 130 Mei Long Road, Shanghai 200237, People's Republic of China.
State Key Laboratory and Institute of Elemento-organic Chemistry, Nankai University , Tianjin 300071, People's Republic of China.
出版信息
Org Lett. 2017 May 5;19(9):2382-2385. doi: 10.1021/acs.orglett.7b00910. Epub 2017 Apr 26.
A [3 + 2] annulation of α-substituted secondary β-ketoamides with δ-acetoxy-modified allenoate has been developed in the presence of phosphine catalyst. In this spiroannulation reaction, β-ketoamides were used as the bis-nucleophilic partner while the γ,δ-carbon of 5-acetoxypenta-2,3-dienoate participated as a C2 synthon, affording the desired functionalized five-membered N-heterocyclic derivatives in moderate to excellent yields and diastereoselectivities under mild conditions. Preliminary attempts on the asymmetric variant of this reaction have been also examined, giving the corresponding products with moderate ee values.
在膦催化剂的存在下，开发了α-取代的次级β-酮酰胺与δ-乙酰氧基修饰的丙二烯酸酯的[3+2]环加成反应。在这个螺环化反应中，β-酮酰胺被用作双亲核试剂，而 5-乙酰氧基戊-2,3-二烯酸酯的γ,δ-碳作为 C2 合成子参与，在温和条件下以中等至优异的收率和非对映选择性得到所需的功能化五元 N-杂环衍生物。该反应的不对称变体的初步尝试也已进行，得到了具有中等 ee 值的相应产物。
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