伯胺催化的吡唑啉-5-酮与α,β-不饱和酮的 1,4-迈克尔对映选择性加成反应

IF 2.2 4区化学 Q2 CHEMISTRY, ORGANIC

Beilstein Journal of Organic Chemistry Pub Date : 2024-07-09 DOI:10.3762/bjoc.20.136

Pooja Goyal, Akhil K. Dubey, Raghunath Chowdhury, Amey Wadawale

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引用次数: 0

摘要

摘要报告了在一种源自金鸡纳生物碱的伯胺–Brøned酸复合体催化下吡唑啉-5-酮与α,β-不饱和酮的对映体选择性1,4-加成反应。在温和的反应条件下，获得了预期的吡唑衍生物的两种对映体，收率从好到极好（高达 97%），对映选择性高（高达 98.5% ee）。此外，该方案还进一步扩展到合成具有生物相关杂环的高对映体杂化分子。Chem.2024, 20, 1518–1526. doi:10.3762/bjoc.20.136

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Primary amine-catalyzed enantioselective 1,4-Michael addition reaction of pyrazolin-5-ones to α,β-unsaturated ketones

Abstract

The enantioselective 1,4-addition reaction of pyrazolin-5-ones to α,β-unsaturated ketones catalyzed by a cinchona alkaloid-derived primary amine–Brønsted acid composite is reported. Both enantiomers of the anticipated pyrazole derivatives were obtained in good to excellent yields (up to 97%) and high enantioselectivities (up to 98.5% ee) under mild reaction conditions. In addition, this protocol was further expanded to synthesize highly enantioenriched hybrid molecules bearing biologically relevant heterocycles.

Beilstein J. Org. Chem. 2024, 20, 1518–1526. doi:10.3762/bjoc.20.136

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来源期刊

Beilstein Journal of Organic Chemistry 化学-有机化学

CiteScore

4.90

自引率

3.70%

发文量

167

审稿时长

1.4 months

期刊介绍： The Beilstein Journal of Organic Chemistry is an international, peer-reviewed, Open Access journal. It provides a unique platform for rapid publication without any charges (free for author and reader) – Platinum Open Access. The content is freely accessible 365 days a year to any user worldwide. Articles are available online immediately upon publication and are publicly archived in all major repositories. In addition, it provides a platform for publishing thematic issues (theme-based collections of articles) on topical issues in organic chemistry. The journal publishes high quality research and reviews in all areas of organic chemistry, including organic synthesis, organic reactions, natural product chemistry, structural investigations, supramolecular chemistry and chemical biology.