Rh(III)催化的烯基羧酸的Ipso和远程氢酰胺化反应以获得有价值的β-氨基酸。

IF 5 1区 化学 Q1 CHEMISTRY, ORGANIC
Shuaikai Ding, Jinlin Liu, Chengkai Bu and Liangbin Huang*, 
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引用次数: 0

摘要

β-氨基酸通常是许多天然产物的关键成分,具有重要的药理特性,并作为各种生物活性化合物的前体。在此,我们提出了一种高效的铑催化的烯基羧酸与HBpin和二恶唑酮的远距离氢酰胺化,以优异的区域选择性(>20:1 rr)获得一系列β-氨基酸,收率高(高达96%)。区域选择性过程进一步强调了这种转化的重要性,该过程使烯基羧酸的异构体混合物能够合成β-氨基酸。此外,该方案成功地将廉价和生物质衍生的羧酸,如油酸和油酸,转化为相应的有价值的β-氨基酸。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Rh(III)-Catalyzed Ipso and Remote Hydroamidation of Alkenyl Carboxylic Acids to Access Valuable β-Amino Acids

Rh(III)-Catalyzed Ipso and Remote Hydroamidation of Alkenyl Carboxylic Acids to Access Valuable β-Amino Acids

β-Amino acids frequently serve as key components in many natural products with significant pharmacological properties and act as precursors to various biologically active compounds. Herein, we present an efficient rhodium-catalyzed ipso and remote hydroamidation of alkenyl carboxylic acids with HBpin and dioxazolones, accessing a series of β-amino acids in good to high yields (up to 96%) with excellent regioselectivity (>20:1 rr). The significance of this transformation is further highlighted by the regioselective process, which enables the synthesis of β-amino acids from isomeric mixtures of alkenyl carboxylic acids. Furthermore, this protocol successfully converts inexpensive and biomass-derived carboxylic acids, such as oleic and elaidic acids, to the corresponding valuable β-amino acids.

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来源期刊
Organic Letters
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.
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