Rapid Access to Densely Functionalized Cyclopentenyl Sulfoximines through a Sc-Catalyzed Aza-Piancatelli Reaction,Organic Letters

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Rapid Access to Densely Functionalized Cyclopentenyl Sulfoximines through a Sc-Catalyzed Aza-Piancatelli Reaction
Organic Letters ( IF 4.9 ) Pub Date : 2024-01-08 , DOI: 10.1021/acs.orglett.3c04095
Emilie Werner ₁ , Milena Wiegand ₁ , Joseph Moran _{1,

2,

3} , David Lebœuf ₁

Affiliation

Sulfoximines make up a class of compounds of growing interest for crop science and medicinal chemistry, but methods for directly incorporating them into complex molecular scaffolds are lacking. Here we report a scandium-catalyzed variant of the aza-Piancatelli cyclization that can directly incorporate sulfoximines as nucleophiles rather than the classical aniline substrates. Starting from 2-furylcarbinols and sulfoximines, the reaction provides direct access to 4-sulfoximinocyclopentenones, a new scaffold bearing cyclopentenone and sulfoximine motifs, both of interest for bioactive compounds.

中文翻译：

通过 Sc 催化的 Aza-Piancatelli 反应快速获得稠密功能化的环戊烯亚磺酰亚胺

亚磺酰亚胺是作物科学和药物化学领域越来越感兴趣的一类化合物，但缺乏将它们直接整合到复杂分子支架中的方法。在这里，我们报道了一种钪催化的氮杂-Piancatelli环化变体，它可以直接将亚砜亚胺作为亲核试剂而不是经典的苯胺底物掺入。从 2-呋喃基甲醇和亚砜亚胺开始，该反应可直接获得 4-亚磺酰亚氨基环戊烯酮，这是一种带有环戊烯酮和亚砜亚胺基序的新支架，这两种基序都是生物活性化合物所感兴趣的。

更新日期：2024-01-08

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