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协同铜/钯催化的多组分反应实现α-季碳手性β-内酰胺的模块化合成。

Modular Synthesis of α-Quaternary Chiral β-Lactams by a Synergistic Copper/Palladium-Catalyzed Multicomponent Reaction.

机构信息

Department of Chemistry, Shandong University, No. 27 South Shanda Road, Jinan, 250100, China.

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China.

出版信息

Angew Chem Int Ed Engl. 2021 Jun 14;60(25):13814-13818. doi: 10.1002/anie.202100601. Epub 2021 May 13.

DOI:10.1002/anie.202100601
PMID:33817889
Abstract

An asymmetric multicomponent, interrupted Kinugasa allylic alkylation (IKAA) reaction has been developed with a synergistic Cu-catalyzed Kinugasa system and a Pd-catalyzed allylic alkylation reaction. This unprecedented reaction provides in high yields and with high stereoselectivity a synthesis of α-quaternary chiral β-lactams, which cannot be produced with existing synthetic methods. Stereoselective coupling of two catalytic amounts of transient organometallic intermediates formed in situ is an important feature of this reaction.

摘要

已开发出一种不对称多组分、间歇 Kinugasa 烯丙基烷基化(IKAA)反应,该反应采用协同的 Cu 催化 Kinugasa 体系和 Pd 催化烯丙基烷基化反应。这种前所未有的反应以高产率和高立体选择性提供了α-季碳手性β-内酰胺的合成,这是现有合成方法无法实现的。两个催化量的瞬态有机金属中间体在原位形成的立体选择性偶联是该反应的一个重要特征。

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