Zn(II)-Catalyzed Asymmetric Reactions of Aminocyclopropanes: (3 + 2) Cycloaddition with Thioketones and Ring Opening with Thioureas.

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-07-16 DOI:10.1021/acs.orglett.5c02071

Xiao-Bing Wang,Cui-Mei Guo,Ming-Sheng Xie,Hai-Ming Guo

引用次数: 0

Abstract

Using C1-symmetric imidazolidine-pyrroloimidazolone-pyridine as a ligand and Zn(OTf)2 as a Lewis acid, an asymmetric (3 + 2)-cyclization reaction of donor-acceptor aminocyclopropanes and thioketones was carried out, providing tetrahydrothiophene derivatives in up to 99% yield, with up to >20:1 dr and 87-99% ee. Additionally, an asymmetric ring opening reaction between aminocyclopropane and substituted thioureas yielded sulfur-containing acyclic compounds with up to 99% yield and up to 96% ee. Furthermore, the origin of the high stereoselectivity was elucidated by control experiments and X-ray crystallography of the chiral Zn(OTf)2-ligand complex.

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Zn（II）催化氨基环丙烷的不对称反应：与硫酮的（3 + 2）环加成和与硫脲的开环反应。

以c1 -对称咪唑烷-吡咯-咪唑酮-吡啶为配体，Zn(OTf)2为Lewis酸，对氨基环丙烷和硫酮进行了不对称（3 + 2）环化反应，得到了收率高达99%的四氢噻吩衍生物，收率高达>20:1 dr， ee高达87-99%。此外，氨基环丙烷和取代硫脲之间的不对称开环反应产生了含硫无环化合物，收率高达99%，ee高达96%。此外，通过对照实验和手性Zn(OTf)2-配体配合物的x射线晶体学分析，阐明了高立体选择性的来源。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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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.