高价碘介导的 2-(4-羟基苯甲酰胺基)丙烯酸酯的螺环化反应——δ-螺内酯的意外形成。
A hypervalent iodine-mediated spirocyclization of 2-(4-hydroxybenzamido)acrylates--unexpected formation of δ-spirolactones.
机构信息
Eberhard Karls University, Institute of Organic Chemistry, Auf der Morgenstelle 18, Tuebingen, Germany.
出版信息
Org Biomol Chem. 2012 Dec 21;10(47):9325-9. doi: 10.1039/c2ob26815a. Epub 2012 Nov 1.
On the way towards a new total synthesis of (S)-arogenate, a novel aryl-λ(3)-iodane-mediated oxidative spirocyclization of para-substituted phenol derivatives has been discovered. Starting from easy accessible 2-(4-hydroxybenzamido)acrylates we could construct spirocyclic lactams in up to 52% yield. Under alternative reaction conditions the same precursors underwent an unexpected oxidative spirocyclization yielding a novel δ-spirolactone in up to 70% yield.
在通往（S）-阿罗加特全新全合成的道路上，我们发现了一种新型的芳基-λ(3)-碘烷介导的对取代苯酚衍生物的氧化螺环化反应。以易得的 2-(4-羟基苯甲酰胺基)丙烯酰胺为起始原料，我们可以构建螺环内酰胺，最高收率为 52%。在替代反应条件下，相同的前体经历了意想不到的氧化螺环化，以高达 70%的收率生成了一种新型的δ-螺内酯。
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