Modular Construction of Chiral Aminopiperidine via Palladium-Catalyzed Hydroamination of 1,2-Dihydropyridine

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-02-12 DOI:10.1021/acs.orglett.4c04736

Qian Wang, Shunshun Huang, Lifei Nie, Jiangyu Zhao, Haji Akber Aisa, Liyin Jiang

引用次数: 0

Abstract

In this study, we describe a generally straightforward methodology for the catalytic synthesis of chiral aminopiperidine from pyridine and azoles. The key step was the palladium-catalyzed regioselective N–H insertion into the double bond of 1,2-dihydropyridine. This hydroamination exhibits a wide substrate scope and functional group compatibility. Mechanistic study revealed that the catalytic N–H insertion into the C═C bond followed cis addition. The utility of this protocol was demonstrated by diverse functionalization of the enamine double bond.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.