通过镍催化醛与受保护氨基戊二烯酸酯的还原偶联，对映选择性合成vic-氨基乙醇衍生物

IF 14.4 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY Journal of the American Chemical Society Pub Date : 2024-11-22 DOI:10.1021/jacs.4c12002

Thilo Bender, Alois Fürstner

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引用次数: 0

摘要

在镍催化的醛与氨基甲酸酯保护的 5-氨基-2,4-戊二烯酸作为 "推/拉 "二烯的反应中，一种源自 VAPOL 的磷酰胺配体能独特有效地逆转反应的区域化学反应过程；随后的羰基 α-氨基-高烯丙基化反应能以良好的收率和高光学纯度生成反构型的沧胺醇衍生物。该还原偶联反应使用台式稳定的 Ni(0) 前催化剂和 Et3B 作为促进剂，非常方便。

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Enantioselective Synthesis of vic-Aminoalcohol Derivatives by Nickel-Catalyzed Reductive Coupling of Aldehydes with Protected Amino-pentadienoates

A VAPOL-derived phosphoramidite ligand is uniquely effective at reverting the regiochemical course of nickel-catalyzed reactions of aldehydes with carbamate-protected 5-amino-2,4-pentadienoates as “push/pull” dienes; the ensuing carbonyl α-amino-homoallylation reaction affords anti-configured vic-aminoalcohol derivatives in good yields with high optical purity. The reductive coupling is conveniently performed with a bench-stable Ni(0) precatalyst and Et₃B as the promoter.

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来源期刊

Journal of the American Chemical Society 化学-化学综合

CiteScore

24.40

自引率

6.00%

发文量

2398

审稿时长

1.6 months

期刊介绍： The flagship journal of the American Chemical Society, known as the Journal of the American Chemical Society (JACS), has been a prestigious publication since its establishment in 1879. It holds a preeminent position in the field of chemistry and related interdisciplinary sciences. JACS is committed to disseminating cutting-edge research papers, covering a wide range of topics, and encompasses approximately 19,000 pages of Articles, Communications, and Perspectives annually. With a weekly publication frequency, JACS plays a vital role in advancing the field of chemistry by providing essential research.