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通过脱氨基三组分偶联实现有机光氧化还原催化合成非天然α/β氨基酸和肽。

Organophotoredox-Catalyzed Synthesis of Unnatural α/β Amino Acids and Peptides via Deaminative Three-Component Coupling.

作者信息

Das Subhodeep, Rahaman Sk Abdur, Pradhan Kangkan, Jana Ranjan

机构信息

Organic and Medicinal Chemistry Division, CSIR-Indian Institute of Chemical Biology, 4 Raja S. C. Mullick Road, Jadavpur, Kolkata 700032, West Bengal, India.

Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201 002, Uttar Pradesh, India.

出版信息

Org Lett. 2024 Aug 23;26(33):6955-6960. doi: 10.1021/acs.orglett.4c02152. Epub 2024 Aug 13.

Abstract

Herein, we disclose an expedient visible-light-mediated, organophotoredox-catalyzed multicomponent synthesis of unnatural amino acids using a Katritzky salt, glyoxal derivatives, and substituted anilines. Mechanistically, an alkyl radical is generated from the Katritzky salt via a deaminative process that undergoes addition to the -generated imine to furnish α-amino acids in a moderate diastereoisomeric ratio. For the first time, we have demonstrated this deaminative protocol to access substituted β-amino acids from α-amino acid-derived Katritzky salts. Furthermore, α-amino amides are also generated from the corresponding 2-oxoacetamide derivatives.

摘要

在此,我们公开了一种便捷的可见光介导、有机光氧化还原催化的多组分合成非天然氨基酸的方法,该方法使用卡特里茨基盐、乙二醛衍生物和取代苯胺。从机理上讲,卡特里茨基盐通过脱氨基过程产生烷基自由基,该自由基加成到生成的亚胺上,以中等非对映异构体比例提供α-氨基酸。我们首次证明了这种脱氨基方案可从α-氨基酸衍生的卡特里茨基盐获得取代的β-氨基酸。此外,相应的2-氧代乙酰胺衍生物也能生成α-氨基酰胺。

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