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通过乙醛二甲基缩醛在恩德斯三级串联反应中的乙醛

Acetaldehyde in the Enders triple cascade reaction via acetaldehyde dimethyl acetal.

作者信息

Brusa Alessandro, Iapadre Debora, Casacchia Maria Edith, Carioscia Alessio, Giorgianni Giuliana, Magagnano Giandomenico, Pesciaioli Fabio, Carlone Armando

机构信息

Department of Physical and Chemical Sciences, Università degli Studi dell'Aquila, via Vetoio, 67100, L'Aquila, Italy.

IUSS Scuola Universitaria Superiore di Pavia, Palazzo del Broletto, Piazza della Vittoria, 15, 27100, Pavia, Italy.

出版信息

Beilstein J Org Chem. 2023 Aug 24;19:1243-1250. doi: 10.3762/bjoc.19.92. eCollection 2023.

Abstract

Asymmetric organocatalyzed multicomponent reactions represent an important toolbox in the field of organic synthesis to build complex scaffolds starting from simple starting materials. The Enders three-component cascade reaction was a cornerstone in the field and a plethora of organocatalyzed cascade reactions followed. However, acetaldehyde was not shown as a successful reaction partner, probably because of its high reactivity. Herein, we report the Enders-type cascade reaction using acetaldehyde dimethyl acetal, as a masked form of acetaldehyde. This strategy directly converts acetaldehyde, nitroalkenes and enals into stereochemically dense cyclohexenals in good yield and excellent enantioselectivity.

摘要

不对称有机催化多组分反应是有机合成领域中一个重要的工具库,可从简单的起始原料构建复杂的骨架结构。恩德斯三组分串联反应是该领域的基石,随后出现了大量的有机催化串联反应。然而,乙醛并未被证明是一种成功的反应伙伴,这可能是由于其高反应活性。在此,我们报道了使用乙醛二甲醇缩醛作为乙醛的一种掩蔽形式的恩德斯型串联反应。该策略能将乙醛、硝基烯烃和烯醛直接转化为具有良好产率和优异对映选择性的立体化学密集的环己烯醛。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c31b/10477997/48531db6b2eb/Beilstein_J_Org_Chem-19-1243-g004.jpg

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