Synthesis of (±)-amathaspiramide F and discovery of an unusual stereocontrolling element for the [2,3]-Stevens rearrangement.
Synthesis of (±)-amathaspiramide F and discovery of an unusual stereocontrolling element for the [2,3]-Stevens rearrangement.
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DOI：
10.1021/ol4025937
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发表时间：
2013-09
期刊：
影响因子：
5.2
通讯作者：
A. Soheili;U. Tambar
中科院分区：
文献类型：
--
作者：
A. Soheili;U. Tambar
报道了一种通过钯催化的烯丙基胺化/[2，3]-Stevens重排反应合成（±）-氨甲螺酰胺F的方法。[2，3]-Stevens重排反应的非对映选择性受芳环取代模式的控制。这一发现代表了在复杂分子环境中[2，3]-σ迁移重排的一种新的立体控制元件。
A formal total synthesis of (±)-amathaspiramide F through a tandem palladium-catalyzed allylic amination/[2,3]-Stevens rearrangement is reported. The unexpected diastereoselectivity of the [2,3]-Stevens rearrangement was controlled by the substitution patterns of an aromatic ring. This discovery represents a new stereocontrolling element for [2,3]-sigmatropic rearrangements in complex molecular settings.