Enantioselective Organocatalytic Addition of 1,3-Dicarbonyl Compounds to β-Arylvinyl Triflones

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2025-03-19 DOI:10.1021/acs.orglett.5c00412

Michał Kopyt, Jan Dudziński, Michał Barbasiewicz, Piotr Kwiatkowski

引用次数: 0

Abstract

The sulfonyl group is able to polarize adjacent C=C bonds, but strength of the effect considerably varies with sulfonyl substituents (SO₂X). In this report, we present asymmetric organocatalyzed conjugate addition of 1,3-dicarbonyl compounds to β-arylvinyl triflones (ArCH=CHSO₂CF₃). The reaction runs under mild conditions with 5 mol % of tertiary amino-thiourea to afford Michael-type adducts in high yields and enantioselectivities. Comparative experiments reveal that electron-withdrawing properties increase in the series SO₂F ≪ SO₂CF₃ < SO₂C₄F₉, with the latter approaching strength of the nitro group.

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1,3-二羰基化合物在β-芳基乙烯基三氟酮中的对映选择性有机催化加成反应

磺酰基能使相邻的C=C键极化，但不同磺酰基取代基（SO2X）的极化强度有很大差异。在这篇报道中，我们提出了1,3-二羰基化合物在β-芳基乙烯基三氟酮（ArCH=CHSO2CF3）上的不对称有机催化共轭加成。该反应在5摩尔%叔氨基硫脲的温和条件下进行，得到了产率高、对映选择性好的迈克尔型加合物。对比试验表明，SO2F系列≪SO2CF3 <；SO2C4F9，后者接近硝基的强度。

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.