铑催化甲基亚胺C−H烯丙基化/环加成与MBH加合物和醋酸烯丙酯合成桥接和熔融四环

IF 2.8 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry Pub Date : 2025-03-01 DOI:10.1002/ajoc.202400646

Yang Sun , Yiyan Wang , Lijun Zhang , Rui Zhong , Hui Wang

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引用次数: 0

摘要

描述了一种铑催化的级联C−H烯丙基化反应，并与森塔-贝利斯-希尔曼（MBH）加合物和醋酸烯丙酯进行了芳基亚甲基亚胺的外和内[3+2]偶极环加成反应。该工艺操作简单，在空气和潮湿条件下进行效率高，可使不同的桥接和熔融四环体成为单一的非对映体。该反应具有广泛的底物范围和良好的官能团相容性。此外，通过成功的规模放大和综合应用，进一步证明了其实用性。

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Synthesis of Bridged and Fused Tetracycles via Rhodium‐Catalyzed C−H Allylation/Cycloaddition of Azomethine Imines with MBH Adducts and Allyl Acetates

A rhodium‐catalyzed cascade C−H allylation combined with exo‐ and endo‐type [3+2] dipolar cycloaddition of aryl azomethine imines with Morita‐Baylis‐Hillman (MBH) adducts and allyl acetates is described. This process, which is operationally simple and proceeds efficiently in air and moisture under neat conditions, facilitates diverse bridged and fused tetracycles as single diastereomers. The reaction showcases a broad substrate scope and good functional group compatibility. Furthermore, its practicality is further demonstrated through successful scale‐up and synthetic applications.

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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.