Enzo Delalande, Lorenzo Di Terlizzi, Camilla Russo, Carmine Volpe, Stefano Protti, mariateresa giustiniano
While arylazo sulfones have been widely applied as arylating agents, their exploitation for diazenylation reactions has been previously limited to electron-rich alkenes such as styrenes and silyl enol ethers. Herein we optimized a synthetic one-pot protocol to access oxazolyl azo compounds via a selective domino ring-closing/aryldiazenylation sequence by starting from arylazo sulfones and isocyanoacetamides in the presence of Sm(OTf)3 as the Lewis acid. The satisfactory substrate scope and functional group tolerance, along with scale-up reaction both in batch and under continuous flow conditions provide a valuable approach to such a class of heteroaryl azo compounds.
{"title":"Dual Lewis Acid Promoted/Visible Light Driven Preparation of Aryl Diazenyl Oxazoles from Isocyanoacetamides and Arylazo Sulfones","authors":"Enzo Delalande, Lorenzo Di Terlizzi, Camilla Russo, Carmine Volpe, Stefano Protti, mariateresa giustiniano","doi":"10.1002/adsc.202401079","DOIUrl":"https://doi.org/10.1002/adsc.202401079","url":null,"abstract":"While arylazo sulfones have been widely applied as arylating agents, their exploitation for diazenylation reactions has been previously limited to electron-rich alkenes such as styrenes and silyl enol ethers. Herein we optimized a synthetic one-pot protocol to access oxazolyl azo compounds via a selective domino ring-closing/aryldiazenylation sequence by starting from arylazo sulfones and isocyanoacetamides in the presence of Sm(OTf)3 as the Lewis acid. The satisfactory substrate scope and functional group tolerance, along with scale-up reaction both in batch and under continuous flow conditions provide a valuable approach to such a class of heteroaryl azo compounds.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"34 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-10-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142556492","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
A palladium-catalyzed double consecutive C(alkenyl)–H activation/alkyne insertion method utilizing a free carboxylic acid as a directing group in the preparation of functionalized naphthalenes is reported. The reaction mechanism involves a sequence of the C (alkenyl)−H activation/alkyne insertion/1,4-palladium migration/reductive elimination steps. The second alkyne insertion occurred at the phenyl ring of the intermediate generated from the first alkyne insertion via 1,4-palladium migration, which is an uncommon case in typical C–H activation/alkyne insertion chemistry, providing functionalized naphthalene products. Additionally, the kinetic studies and control experiments as well as density functional theory (DFT) studies are also investigated to elucidate the reaction mechanism.
{"title":"Carboxylate-Directed Oxidative Annulation via C(Alkenyl)－H Activation/Double Alkyne Insertion/1,4-Pd Migration: Synthesis of Functionalized Naphthalenes","authors":"Chih-Ming Chou, Cheng-Hao Fu, Manjaly J. Ajitha, Veerabhushanam Kadiyala, Yu-Chun Wang, Tzu-Yu Hsu, I-Hsuan Sung, Kuo-wei Huang","doi":"10.1002/adsc.202400973","DOIUrl":"https://doi.org/10.1002/adsc.202400973","url":null,"abstract":"A palladium-catalyzed double consecutive C(alkenyl)–H activation/alkyne insertion method utilizing a free carboxylic acid as a directing group in the preparation of functionalized naphthalenes is reported. The reaction mechanism involves a sequence of the C (alkenyl)−H activation/alkyne insertion/1,4-palladium migration/reductive elimination steps. The second alkyne insertion occurred at the phenyl ring of the intermediate generated from the first alkyne insertion via 1,4-palladium migration, which is an uncommon case in typical C–H activation/alkyne insertion chemistry, providing functionalized naphthalene products. Additionally, the kinetic studies and control experiments as well as density functional theory (DFT) studies are also investigated to elucidate the reaction mechanism.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"22 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-10-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142562352","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Csaba Árvai, Zoltán Medgyesi, Matthew Yuk-Yu LUI, Laszlo Mika
Biomass has been identified as the ultimate sustainable resource for all carbon-based consumer products of the chemical industries in the future. Its catalytic conversion leads to the formation of various platform chemicals that could partially or even fully replace the fossil-based building blocks that have been currently used in synthetic chemical processes. Among these compounds, levulinic acid (LA) has been recognized as a member of the "Top Value Added Chemicals from Biomass" and has attracted significant attention since the seminal paper reported by Werpy and Petersen in 2004. This review summarizes the properties, recent advances, and developments in the chemistry of levulinic acid. The production of LA from both plant and animal-based carbohydrate feedstocks via 5-hydroxymethylfurfural or furfuryl alcohol is discussed from a mechanistic perspective, highlighting intrinsic molecular-level limitations to LA formation. The efficiencies of recently developed catalytic systems are also summarized and compared. Furthermore, the conversion of LA into high-value-added downstream chemicals, including its role in the synthesis of complex molecular structures, is overviewed. This section discussed the reactions of LA in the points of view of its various transformations on carbonyl-, carboxy-, methyl-, and methylene functional groups. The reactions of these functionalities with C- ,N-, O-, and S-nucleophiles, alcohols, amines, organometallic reagents, oxygen etc. were thematically summarized. Our review also outlooks to highlight the challenges and opportunities associated with the extensive research area of organic chemistry of levulinic acid.
生物质被认为是未来化学工业所有碳基消费品的最终可持续资源。生物质在催化转化过程中可生成各种平台化学品，这些化学品可部分甚至完全取代目前合成化学工艺中使用的化石基构件。在这些化合物中，乙酰丙酸（LA）已被公认为 "生物质高附加值化学品 "中的一员，自 Werpy 和 Petersen 于 2004 年发表开创性论文以来，它一直备受关注。本综述总结了乙酰丙酸的特性、最新进展和化学发展。从机理的角度讨论了通过 5-羟甲基糠醛或糠醇从植物和动物基碳水化合物原料中生产 LA 的过程，强调了 LA 形成过程中固有的分子水平限制。还总结并比较了最近开发的催化系统的效率。此外，还概述了将 LA 转化为高附加值下游化学品的过程，包括其在合成复杂分子结构中的作用。本节从羰基、羧基、甲基和亚甲基官能团的各种转化角度讨论了 LA 的反应。专题总结了这些官能团与 C-、N-、O- 和 S-亲核物、醇、胺、有机金属试剂、氧等的反应。我们的综述还展望了与乙酰丙酸有机化学这一广泛研究领域相关的挑战和机遇。
{"title":"The Chemistry of Levulinic Acid: Its Potential in the Production of Biomass-based Chemicals","authors":"Csaba Árvai, Zoltán Medgyesi, Matthew Yuk-Yu LUI, Laszlo Mika","doi":"10.1002/adsc.202401086","DOIUrl":"https://doi.org/10.1002/adsc.202401086","url":null,"abstract":"Biomass has been identified as the ultimate sustainable resource for all carbon-based consumer products of the chemical industries in the future. Its catalytic conversion leads to the formation of various platform chemicals that could partially or even fully replace the fossil-based building blocks that have been currently used in synthetic chemical processes. Among these compounds, levulinic acid (LA) has been recognized as a member of the \"Top Value Added Chemicals from Biomass\" and has attracted significant attention since the seminal paper reported by Werpy and Petersen in 2004. This review summarizes the properties, recent advances, and developments in the chemistry of levulinic acid. The production of LA from both plant and animal-based carbohydrate feedstocks via 5-hydroxymethylfurfural or furfuryl alcohol is discussed from a mechanistic perspective, highlighting intrinsic molecular-level limitations to LA formation. The efficiencies of recently developed catalytic systems are also summarized and compared. Furthermore, the conversion of LA into high-value-added downstream chemicals, including its role in the synthesis of complex molecular structures, is overviewed. This section discussed the reactions of LA in the points of view of its various transformations on carbonyl-, carboxy-, methyl-, and methylene functional groups. The reactions of these functionalities with C- ,N-, O-, and S-nucleophiles, alcohols, amines, organometallic reagents, oxygen etc. were thematically summarized. Our review also outlooks to highlight the challenges and opportunities associated with the extensive research area of organic chemistry of levulinic acid.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"32 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-10-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142556455","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Shabbir Muhammad, Li Zeng, Hao Li, Aiwen Lei, Hong Yi
Quinoxaline is a chemical moiety known for its diverse physicochemical and biological properties, making it the focus of extensive research. Over the past few decades, quinoxaline scaffolds have been utilized in the design and development of various bioactive molecules, dyes, fluorescent materials, electroluminescent materials, organic sensitizers for solar cells, and polymeric optoelectronic materials. Herein, we present a metal-free and rapid protocol for the phosphorylation of quinoxalines and quinoxalin-2(1H)-one. This method employs oxygen as an oxidant under ambient temperature and atmospheric pressure, with experimental evidence indicating the absence of radical involvement. Our methodology provides range of phosphorylated quinoxalines and quinoxaline-2(1H)-one in yields ranging from 47% to 99%.
{"title":"Acid-Mediated Oxidative C-H Phosphorylation of Quinoxalines and Quinoxalin-2(1H)-one","authors":"Shabbir Muhammad, Li Zeng, Hao Li, Aiwen Lei, Hong Yi","doi":"10.1002/adsc.202401081","DOIUrl":"https://doi.org/10.1002/adsc.202401081","url":null,"abstract":"Quinoxaline is a chemical moiety known for its diverse physicochemical and biological properties, making it the focus of extensive research. Over the past few decades, quinoxaline scaffolds have been utilized in the design and development of various bioactive molecules, dyes, fluorescent materials, electroluminescent materials, organic sensitizers for solar cells, and polymeric optoelectronic materials. Herein, we present a metal-free and rapid protocol for the phosphorylation of quinoxalines and quinoxalin-2(1H)-one. This method employs oxygen as an oxidant under ambient temperature and atmospheric pressure, with experimental evidence indicating the absence of radical involvement. Our methodology provides range of phosphorylated quinoxalines and quinoxaline-2(1H)-one in yields ranging from 47% to 99%.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"87 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-10-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142542148","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Karl Scheidt, Matthew McGill, Cullen Schull, Adam Wayment
α-Aryl glycines are among the more important carbonyl compounds, particularly as nonproteinogenic α-amino acids present in many pharmacophores. As such, many strategies have been developed to access this motif, but direct carboxylation methods remain underdeveloped. Herein, we employ a dual NHC/HAT catalysis strategy to access 2-azaallyl radicals, which subsequently couple with in situ generated ester azolium radical intermediates. Base-mediated collapse of the ensuing tetrahedral intermediate liberates the NHC catalyst and benzophenone protected aryl glycine. This methodology was employed to esterify obtain a variety of aryl substituted glycine derivatives, as well as allylic and benzylic sites. Mechanistic studies reveal that this radical process operates under both oxidative and reductive quenching cycles, while preliminary experiments employing a chiral NHC and Lewis acid additive demonstrate modest enantioselectivity.
{"title":"Dual NHC/HAT-Promoted Esterification to Access α-Aryl Glycines","authors":"Karl Scheidt, Matthew McGill, Cullen Schull, Adam Wayment","doi":"10.1002/adsc.202401207","DOIUrl":"https://doi.org/10.1002/adsc.202401207","url":null,"abstract":"α-Aryl glycines are among the more important carbonyl compounds, particularly as nonproteinogenic α-amino acids present in many pharmacophores. As such, many strategies have been developed to access this motif, but direct carboxylation methods remain underdeveloped. Herein, we employ a dual NHC/HAT catalysis strategy to access 2-azaallyl radicals, which subsequently couple with in situ generated ester azolium radical intermediates. Base-mediated collapse of the ensuing tetrahedral intermediate liberates the NHC catalyst and benzophenone protected aryl glycine. This methodology was employed to esterify obtain a variety of aryl substituted glycine derivatives, as well as allylic and benzylic sites. Mechanistic studies reveal that this radical process operates under both oxidative and reductive quenching cycles, while preliminary experiments employing a chiral NHC and Lewis acid additive demonstrate modest enantioselectivity.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"16 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-10-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142542151","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
In this work, we extend the one-pot protocol to synthesize 1,2-diazepines from commercially available and cheap starting materials. Capitalizing on isocyanate derivatives as activating agents, the photochemical skeletal enlargement occurs, while preserving key functional groups embedded in more than 30 substrates. We also demonstrated that isocyanates can be generated in situ exploiting the wealth of methods starting from bench stable resources. Compare to previous strategies, the use of these precursors prevents the presence of deleterious HCl traces in the system, thus enabling the synthesis of 1,2-diazepines in high yields over up to 5 sequential steps.
{"title":"Improving the Photochemical Skeletal Enlargement of Pyridines to 1,2-Diazepines with Isocyanates","authors":"Clément Ghiazza, Aurélie Damond, Jérome Marrot, Xavier Moreau","doi":"10.1002/adsc.202401201","DOIUrl":"https://doi.org/10.1002/adsc.202401201","url":null,"abstract":"In this work, we extend the one-pot protocol to synthesize 1,2-diazepines from commercially available and cheap starting materials. Capitalizing on isocyanate derivatives as activating agents, the photochemical skeletal enlargement occurs, while preserving key functional groups embedded in more than 30 substrates. We also demonstrated that isocyanates can be generated in situ exploiting the wealth of methods starting from bench stable resources. Compare to previous strategies, the use of these precursors prevents the presence of deleterious HCl traces in the system, thus enabling the synthesis of 1,2-diazepines in high yields over up to 5 sequential steps.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"44 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-10-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142542152","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Rodrigo Costa, Gabriel M. F. Batista, Timothy J Brocksom, Kleber de Oliveira
Herein, we report a multidimensional screening strategy to discover Electron Donor-Acceptor (EDA) complex photochemical reactions using only simple photographic devices, such as webcams or cellphones, combined with TLC analysis. An algorithm was designed to automatically identify EDA-complex reactive mixtures in solution by processing digital images from a 96-well microplate, alongside TLC results. The code detects the absorption region of the mixture in the visible spectrum and quantifies color changes through grayscale values. Integrated automatic TLC analysis further classifies mixtures as colorimetric reactions, non-reactive, or potentially reactive EDA complexes. Leveraging this screening platform, we have developed a new EDA-mediated approach to synthesize iminophosphoranes in yields up to 90%.
{"title":"Discovery of EDA-Complex Photochemical Reactions Using Computational Vision","authors":"Rodrigo Costa, Gabriel M. F. Batista, Timothy J Brocksom, Kleber de Oliveira","doi":"10.1002/adsc.202401045","DOIUrl":"https://doi.org/10.1002/adsc.202401045","url":null,"abstract":"Herein, we report a multidimensional screening strategy to discover Electron Donor-Acceptor (EDA) complex photochemical reactions using only simple photographic devices, such as webcams or cellphones, combined with TLC analysis. An algorithm was designed to automatically identify EDA-complex reactive mixtures in solution by processing digital images from a 96-well microplate, alongside TLC results. The code detects the absorption region of the mixture in the visible spectrum and quantifies color changes through grayscale values. Integrated automatic TLC analysis further classifies mixtures as colorimetric reactions, non-reactive, or potentially reactive EDA complexes. Leveraging this screening platform, we have developed a new EDA-mediated approach to synthesize iminophosphoranes in yields up to 90%.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"544 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-10-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142541959","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
We describe a fluorinative ring-cleavage reaction that breaks C–C bonds in cyclic β-diketones bearing aryl moiety using N-fluorobenzenesulfonimide (NFSI) in the presence of inorganic carbonates (Cs2CO3 or K2CO3) in methanol at room temperature within one hour. Generated fluorinated keto acid esters bearing ortho-nitro aryl groups were transformed into fluorinated dihydropyrido[1,2-a]indolones (DHPIs) via reductive cyclization using B2(OH)4 followed by amidation in the presence of K2CO3. This "cut-to-fuse" strategy enables the reconstructive synthesis of valuable fused heterocycles from relatively simple cyclohexadione.
{"title":"Reconstructive synthesis of fluorinated dihydropyrido[1,2-a]indolones by a cyclohexadione cut-to-fuse strategy","authors":"Hideyasu China, Yusuke Yoto, Hirotaka Sasa, Kotaro Kikushima, Toshifumi Dohi","doi":"10.1002/adsc.202401037","DOIUrl":"https://doi.org/10.1002/adsc.202401037","url":null,"abstract":"We describe a fluorinative ring-cleavage reaction that breaks C–C bonds in cyclic β-diketones bearing aryl moiety using N-fluorobenzenesulfonimide (NFSI) in the presence of inorganic carbonates (Cs2CO3 or K2CO3) in methanol at room temperature within one hour. Generated fluorinated keto acid esters bearing ortho-nitro aryl groups were transformed into fluorinated dihydropyrido[1,2-a]indolones (DHPIs) via reductive cyclization using B2(OH)4 followed by amidation in the presence of K2CO3. This \"cut-to-fuse\" strategy enables the reconstructive synthesis of valuable fused heterocycles from relatively simple cyclohexadione.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"118 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-10-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142519970","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Vincent Gandon, Aurélien Alix, Nicolas S. George, Régis Guillot, Emilie Kolodziej, Christophe Bour, Xiangmeng Chen
A series of 4-sulfoximinocyclopent-2-en-1-ones were prepared in 35 to 99% yield through a calcium(II)-catalyzed aza-Piancatelli reaction, including in enantioenriched form. Depending on their substitution pattern, diverse diastereoselective chemical transformations can be applied to these scaffolds, allowing access to cyclopentane derivatives. This study opens synthetic routes to cyclopentane-based scaffolds and also paves the way for the exploration of the associated chemical space in drug discovery.
{"title":"Calcium(II)-Catalyzed Synthesis of Sulfoximinocyclopentenones","authors":"Vincent Gandon, Aurélien Alix, Nicolas S. George, Régis Guillot, Emilie Kolodziej, Christophe Bour, Xiangmeng Chen","doi":"10.1002/adsc.202401085","DOIUrl":"https://doi.org/10.1002/adsc.202401085","url":null,"abstract":"A series of 4-sulfoximinocyclopent-2-en-1-ones were prepared in 35 to 99% yield through a calcium(II)-catalyzed aza-Piancatelli reaction, including in enantioenriched form. Depending on their substitution pattern, diverse diastereoselective chemical transformations can be applied to these scaffolds, allowing access to cyclopentane derivatives. This study opens synthetic routes to cyclopentane-based scaffolds and also paves the way for the exploration of the associated chemical space in drug discovery.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"23 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-10-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142519959","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Deuterated hydroxyl acids and amino acids have been widely utilized in life science, biochemistry and drug development. Site-selective and stereoselective synthesis of deuterated hydroxyl acids and amino acids remains a significant challenge. Here, we report the development of a robust whole-cell-based chemoenzymatic platform for the synthesis of deuterated hydroxyl acids and amino acids from off-the-shelf aldehydes in high yields with excellent selectivities and levels of deuteration. The platform delivers products with diverse scaffolds and deuteration patterns, as well as broad scopes with both aromatic and aliphatic side chains. The application of the platform was demonstrated by the concise synthesis of a deuterium-containing antiparkinson's disease candidate. This platform provides a concrete foundation for accessing amino acid isotopologs for potential applications in research and drug discovery and development.
{"title":"Robust whole-cell-based chemoenzymatic synthesis of site-selective deuterated α-hydroxy acids and α-amino acids","authors":"Cangsong Liao","doi":"10.1002/adsc.202401330","DOIUrl":"https://doi.org/10.1002/adsc.202401330","url":null,"abstract":"Deuterated hydroxyl acids and amino acids have been widely utilized in life science, biochemistry and drug development. Site-selective and stereoselective synthesis of deuterated hydroxyl acids and amino acids remains a significant challenge. Here, we report the development of a robust whole-cell-based chemoenzymatic platform for the synthesis of deuterated hydroxyl acids and amino acids from off-the-shelf aldehydes in high yields with excellent selectivities and levels of deuteration. The platform delivers products with diverse scaffolds and deuteration patterns, as well as broad scopes with both aromatic and aliphatic side chains. The application of the platform was demonstrated by the concise synthesis of a deuterium-containing antiparkinson's disease candidate. This platform provides a concrete foundation for accessing amino acid isotopologs for potential applications in research and drug discovery and development.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"237 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-10-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142519921","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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