Single step synthesis of β- and γ- aryl-substituted ß- and γ-amino acid derivatives by electrochemistry
[Display omitted] Electrochemical transformations are a subject of increasing interest in early drug discovery due to its ability to assemble complex scaffolds under rather mild reaction conditions. In this context, we became interested in electrochemical decarboxylative cross-coupling (DCC) protoco...
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Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2024-03, Vol.100, p.129614-129614, Article 129614 |
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container_title | Bioorganic & medicinal chemistry letters |
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creator | Pavlovic, Barbara Heubel, Christoph Kurz, Michael Oehl, Elisabeth Waldvogel, Siegfried R. Méndez, Maria Ruf, Sven |
description | [Display omitted]
Electrochemical transformations are a subject of increasing interest in early drug discovery due to its ability to assemble complex scaffolds under rather mild reaction conditions. In this context, we became interested in electrochemical decarboxylative cross-coupling (DCC) protocols of redox-active esters (RAEs) and halo(hetero)arenes. Starting with the one-step electrochemical synthesis of novel methylamino-substituted heterocycles we recognized the potential of this methodology to deliver a novel approach to β- and γ- amino acids by starting from the corresponding RAEs. Our work finally resulted in the delivery of novel and highly valuable trifunctional building blocks based on ß- and γ-amino-acid scaffolds. |
doi_str_mv | 10.1016/j.bmcl.2024.129614 |
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Electrochemical transformations are a subject of increasing interest in early drug discovery due to its ability to assemble complex scaffolds under rather mild reaction conditions. In this context, we became interested in electrochemical decarboxylative cross-coupling (DCC) protocols of redox-active esters (RAEs) and halo(hetero)arenes. Starting with the one-step electrochemical synthesis of novel methylamino-substituted heterocycles we recognized the potential of this methodology to deliver a novel approach to β- and γ- amino acids by starting from the corresponding RAEs. Our work finally resulted in the delivery of novel and highly valuable trifunctional building blocks based on ß- and γ-amino-acid scaffolds.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2024.129614</identifier><identifier>PMID: 38199329</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>DCC coupling ; Electrochemistry ; Nickel catalyzed ; Trifunctional building blocks ; ß-amino acid ; γ-aminoacid</subject><ispartof>Bioorganic & medicinal chemistry letters, 2024-03, Vol.100, p.129614-129614, Article 129614</ispartof><rights>2024</rights><rights>Copyright © 2024. Published by Elsevier Ltd.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c356t-17723fdf3ec87b1416b3e249ba1bfbdb66de16a7cf5d92aa16dfa9ec1e2bfd2c3</citedby><cites>FETCH-LOGICAL-c356t-17723fdf3ec87b1416b3e249ba1bfbdb66de16a7cf5d92aa16dfa9ec1e2bfd2c3</cites><orcidid>0000-0002-6832-2714</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmcl.2024.129614$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>315,781,785,3551,27929,27930,46000</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/38199329$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Pavlovic, Barbara</creatorcontrib><creatorcontrib>Heubel, Christoph</creatorcontrib><creatorcontrib>Kurz, Michael</creatorcontrib><creatorcontrib>Oehl, Elisabeth</creatorcontrib><creatorcontrib>Waldvogel, Siegfried R.</creatorcontrib><creatorcontrib>Méndez, Maria</creatorcontrib><creatorcontrib>Ruf, Sven</creatorcontrib><title>Single step synthesis of β- and γ- aryl-substituted ß- and γ-amino acid derivatives by electrochemistry</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>[Display omitted]
Electrochemical transformations are a subject of increasing interest in early drug discovery due to its ability to assemble complex scaffolds under rather mild reaction conditions. In this context, we became interested in electrochemical decarboxylative cross-coupling (DCC) protocols of redox-active esters (RAEs) and halo(hetero)arenes. Starting with the one-step electrochemical synthesis of novel methylamino-substituted heterocycles we recognized the potential of this methodology to deliver a novel approach to β- and γ- amino acids by starting from the corresponding RAEs. Our work finally resulted in the delivery of novel and highly valuable trifunctional building blocks based on ß- and γ-amino-acid scaffolds.</description><subject>DCC coupling</subject><subject>Electrochemistry</subject><subject>Nickel catalyzed</subject><subject>Trifunctional building blocks</subject><subject>ß-amino acid</subject><subject>γ-aminoacid</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNp9kE1uUzEUhS0EomlhAwyQh0xe6ms7Tix1gqpCK1XqAJA6s_xzTR3eT7D9ImU17KEsgXnX1Bel7ZDRGdxzztX5CPkAbA4M1Ol67jrfzjnjcg5cK5CvyAykko2QbPGazJhWrFlpeXtEjktZMwaSSfmWHIkVaC24npFf31L_s0VaKm5o2fX1DksqdIj04b6htg_04e-kedc2ZXSlpjpWDPTfn5ej7VI_UOtToAFz2tqatlio21Fs0dc8-DvsUql59468ibYt-P5JT8iPLxffzy-b65uvV-efrxsvFqo2sFxyEUMU6FdLBxKUE8ildhZcdMEpFRCUXfq4CJpbCypEq9EDchcD9-KEfDr0bvLwe8RSzfTfY9vaHoexGK5BSKmV4pOVH6w-D6VkjGaTUzfNNcDMHrJZmz1ks4dsDpCn0Men_tF1GF4iz1Qnw9nBgNPKbcJsik_YewwpT0hMGNL_-h8BCpiSfA</recordid><startdate>20240301</startdate><enddate>20240301</enddate><creator>Pavlovic, Barbara</creator><creator>Heubel, Christoph</creator><creator>Kurz, Michael</creator><creator>Oehl, Elisabeth</creator><creator>Waldvogel, Siegfried R.</creator><creator>Méndez, Maria</creator><creator>Ruf, Sven</creator><general>Elsevier Ltd</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-6832-2714</orcidid></search><sort><creationdate>20240301</creationdate><title>Single step synthesis of β- and γ- aryl-substituted ß- and γ-amino acid derivatives by electrochemistry</title><author>Pavlovic, Barbara ; Heubel, Christoph ; Kurz, Michael ; Oehl, Elisabeth ; Waldvogel, Siegfried R. ; Méndez, Maria ; Ruf, Sven</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c356t-17723fdf3ec87b1416b3e249ba1bfbdb66de16a7cf5d92aa16dfa9ec1e2bfd2c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>DCC coupling</topic><topic>Electrochemistry</topic><topic>Nickel catalyzed</topic><topic>Trifunctional building blocks</topic><topic>ß-amino acid</topic><topic>γ-aminoacid</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Pavlovic, Barbara</creatorcontrib><creatorcontrib>Heubel, Christoph</creatorcontrib><creatorcontrib>Kurz, Michael</creatorcontrib><creatorcontrib>Oehl, Elisabeth</creatorcontrib><creatorcontrib>Waldvogel, Siegfried R.</creatorcontrib><creatorcontrib>Méndez, Maria</creatorcontrib><creatorcontrib>Ruf, Sven</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Pavlovic, Barbara</au><au>Heubel, Christoph</au><au>Kurz, Michael</au><au>Oehl, Elisabeth</au><au>Waldvogel, Siegfried R.</au><au>Méndez, Maria</au><au>Ruf, Sven</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Single step synthesis of β- and γ- aryl-substituted ß- and γ-amino acid derivatives by electrochemistry</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2024-03-01</date><risdate>2024</risdate><volume>100</volume><spage>129614</spage><epage>129614</epage><pages>129614-129614</pages><artnum>129614</artnum><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>[Display omitted]
Electrochemical transformations are a subject of increasing interest in early drug discovery due to its ability to assemble complex scaffolds under rather mild reaction conditions. In this context, we became interested in electrochemical decarboxylative cross-coupling (DCC) protocols of redox-active esters (RAEs) and halo(hetero)arenes. Starting with the one-step electrochemical synthesis of novel methylamino-substituted heterocycles we recognized the potential of this methodology to deliver a novel approach to β- and γ- amino acids by starting from the corresponding RAEs. Our work finally resulted in the delivery of novel and highly valuable trifunctional building blocks based on ß- and γ-amino-acid scaffolds.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>38199329</pmid><doi>10.1016/j.bmcl.2024.129614</doi><tpages>1</tpages><orcidid>https://orcid.org/0000-0002-6832-2714</orcidid></addata></record> |
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subjects | DCC coupling Electrochemistry Nickel catalyzed Trifunctional building blocks ß-amino acid γ-aminoacid |
title | Single step synthesis of β- and γ- aryl-substituted ß- and γ-amino acid derivatives by electrochemistry |
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