Pd(0)/InI-Mediated Allylic Additions to 4-Acetoxy-2-azetidinone: New Route to Highly Functionalized Carbocyclic Scaffolds
Pd(0)/InI-Mediated Allylic Additions to 4-Acetoxy-2-azetidinone: New Route to Highly Functionalized Carbocyclic Scaffolds
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DOI：
10.1021/ol9000685
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发表时间：
2009-03-19
期刊：
影响因子：
5.2
通讯作者：
Miller, Marvin J.
中科院分区：
文献类型：
--
作者：
Cesario, Cara;Miller, Marvin J.
酰基亚硝基衍生的杂 Diels-Alder 环加合物易于与 Pd(0) 和 InI 发生 C-O 键断裂，形成烯丙基铟 (III) 物质。原位制备的烯丙基化合物在室温下很容易与Eschenmoser盐反应。 4-乙酰氧基-2-氮杂环丁酮的烯丙基化提供了具有高区域选择性和非对映选择性的衍生环戊烯。
Acylnitroso-derived hetero-Diels-Alder cycloadducts are susceptible to C-O bond cleavage with Pd(0) and InI to form allylic indium(III) species. The in situ prepared allylindium compounds readily react at room temperature with Eschenmoser's salt. Allylation of 4-acetoxy-2-azetidinone provides derivatized cyclopentenes in high regio- and diastereoselectivity.