Iron-Catalyzed Enantioconvergent Amination of Alcohols

IF 15.6 1区 化学 Q1 CHEMISTRY, MULTIDISCIPLINARY
Fan Sun, Bo-Xuan Yao, Siyi Wang, Bolin Ji*, Shao-Fei Ni* and Weiping Liu*, 
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引用次数: 0

Abstract

Owing to the prevalence of chiral amines in natural products and pharmaceuticals, we developed an iron-catalyzed borrowing hydrogen enantioconvergent amination of alcohols in the presence of chiral phosphoric acid. This protocol effectively converts a range of secondary alcohols and amines, tolerating numerous functional groups, including hydroxyl, cyano, ester, and boronate groups, into chiral amines with high to excellent yields (up to 99%) and enantioselectivities (up to 99% ee). Notably, the compatibility with peptides, including di- and tripeptides, offers new possibilities for exploring chemical transformations in biological contexts. Mechanistic studies revealed a hydrogen-borrowing pathway, with DFT calculations further elucidating the crucial role of the chiral environment (pocket) in controlling enantioselectivity.

Abstract Image

铁催化醇的对映收敛胺化反应
由于手性胺在天然产物和药物中的普遍存在,我们在手性磷酸的存在下开发了一种铁催化的借用氢对映收敛胺化醇。该方案有效地将一系列仲醇和胺,耐受许多官能团,包括羟基,氰基,酯和硼酸基团,转化为手性胺,具有高至优异的收率(高达99%)和对映选择性(高达99% ee)。值得注意的是,与肽的相容性,包括二肽和三肽,为探索生物环境中的化学转化提供了新的可能性。机制研究揭示了一个借氢途径,DFT计算进一步阐明了手性环境(口袋)在控制对映体选择性中的关键作用。
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来源期刊
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.
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