Construction of Dihydropyrano[2,3-c]pyrazolone via Photo-induced Wolff Rearrangement/Chiral Isothiourea Catalyzed [4+2] Cyclization Reaction

IF 2.8 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry Pub Date : 2024-08-13 DOI:10.1002/ajoc.202400387

Zhou Zhang, Siyu Shi, Hai Guo, Zhiqiang Shen, Xia Liu, Jinqi Huang, Wenjin Yan

引用次数: 0

Abstract

A photoinduced Wolff rearrangement/chiral isothiourea catalyzed [4+2] cycloaddition reaction of pyrazolone derivatives and α-diazoketones was developed, affording the corresponding dihydropyrano[2,3-c]pyrazolone derivatives in moderate to good yields (50–94 %) with satisfactory to excellent diastereoselectivities (>20 : 1 dr, in almost all cases) and enantioselectivities of 31–99 %. This protocol features readily available substrates, mild reaction conditions, and effective construction of vicinal tertiary and quaternary carbon stereocenters.

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通过光诱导沃尔夫重排/手性异硫脲催化[4+2]环化反应构建二氢吡喃并[2,3-c]吡唑酮

研究人员开发了一种光诱导沃尔夫重排/手性异硫脲催化的吡唑酮衍生物与α-重氮酮的[4+2]环加成反应，得到了相应的二氢吡喃并[2,3-c]吡唑酮衍生物，收率中等至良好（50-94%），非对映选择性令人满意至极佳（几乎在所有情况下均为 20:1），对映选择性为 31-99%。该方法的特点是底物易得、反应条件温和，并能有效地构建邻接的三级和四级碳立体中心。

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来源期刊

Asian Journal of Organic Chemistry CHEMISTRY, ORGANIC-

CiteScore

4.70

自引率

3.70%

发文量

372

期刊介绍： Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC) The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.