Nickel-catalyzed carbodifunctionalization of N-vinylamides enables access to γ-amino acids
A nickel-catalyzed tandem reaction of N-vinylamides with arylboronic acids and bromodifluoroacetate has been developed. The use of amide carbonyl as a chelating group efficiently furnishes a series of protected α,α-difluoro-γ-amino acid esters. The reaction can also extend to bromoacetate and 2-brom...
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| Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2020-02, Vol.56 (17), p.2642-2645 |
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| container_title | Chemical communications (Cambridge, England) |
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| creator | Yang, Zhi-Fang Xu, Chang Zheng, Xing Zhang, Xingang |
| description | A nickel-catalyzed tandem reaction of N-vinylamides with arylboronic acids and bromodifluoroacetate has been developed. The use of amide carbonyl as a chelating group efficiently furnishes a series of protected α,α-difluoro-γ-amino acid esters. The reaction can also extend to bromoacetate and 2-bromomalonate. The advantages of this protocol are high functional group tolerance and a broad substrate scope, including a variety of N-vinylamides. In particular, the use of removable amide carbonyl groups provides potential opportunities for applications in peptide chemistry and protein engineering. |
| doi_str_mv | 10.1039/c9cc09866f |
| format | Article |
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The use of amide carbonyl as a chelating group efficiently furnishes a series of protected α,α-difluoro-γ-amino acid esters. The reaction can also extend to bromoacetate and 2-bromomalonate. The advantages of this protocol are high functional group tolerance and a broad substrate scope, including a variety of N-vinylamides. In particular, the use of removable amide carbonyl groups provides potential opportunities for applications in peptide chemistry and protein engineering.</description><identifier>ISSN: 1359-7345</identifier><identifier>EISSN: 1364-548X</identifier><identifier>DOI: 10.1039/c9cc09866f</identifier><identifier>PMID: 32021998</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Amides - chemistry ; Amino acids ; Amino Acids - chemistry ; Carbonyl groups ; Carbonyls ; Cascade chemical reactions ; Catalysis ; Chelating Agents - chemistry ; Chelation ; Esters ; Functional groups ; Nickel ; Nickel - chemistry ; Organic chemistry ; Substrates</subject><ispartof>Chemical communications (Cambridge, England), 2020-02, Vol.56 (17), p.2642-2645</ispartof><rights>Copyright Royal Society of Chemistry 2020</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c315t-fa12cb8f8af267a24638bd862fec5e70fa1f663913ec7b333061ec525b70aac3</citedby><cites>FETCH-LOGICAL-c315t-fa12cb8f8af267a24638bd862fec5e70fa1f663913ec7b333061ec525b70aac3</cites><orcidid>0000-0002-4406-6533</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/32021998$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Yang, Zhi-Fang</creatorcontrib><creatorcontrib>Xu, Chang</creatorcontrib><creatorcontrib>Zheng, Xing</creatorcontrib><creatorcontrib>Zhang, Xingang</creatorcontrib><title>Nickel-catalyzed carbodifunctionalization of N-vinylamides enables access to γ-amino acids</title><title>Chemical communications (Cambridge, England)</title><addtitle>Chem Commun (Camb)</addtitle><description>A nickel-catalyzed tandem reaction of N-vinylamides with arylboronic acids and bromodifluoroacetate has been developed. The use of amide carbonyl as a chelating group efficiently furnishes a series of protected α,α-difluoro-γ-amino acid esters. The reaction can also extend to bromoacetate and 2-bromomalonate. The advantages of this protocol are high functional group tolerance and a broad substrate scope, including a variety of N-vinylamides. In particular, the use of removable amide carbonyl groups provides potential opportunities for applications in peptide chemistry and protein engineering.</description><subject>Amides - chemistry</subject><subject>Amino acids</subject><subject>Amino Acids - chemistry</subject><subject>Carbonyl groups</subject><subject>Carbonyls</subject><subject>Cascade chemical reactions</subject><subject>Catalysis</subject><subject>Chelating Agents - chemistry</subject><subject>Chelation</subject><subject>Esters</subject><subject>Functional groups</subject><subject>Nickel</subject><subject>Nickel - chemistry</subject><subject>Organic chemistry</subject><subject>Substrates</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpdkM1KAzEUhYMotlY3PoAMuBEhmp9JJlnKYFUoddOF4GLIZBJInU7qZEZoX8v38JnM2OrCuzmXez4O3APAOUY3GFF5q6XWSArO7QEYY8pTyFLxcjjsTMKMpmwETkJYojiYiWMwogQRLKUYg9e502-mhlp1qt5sTZVo1Za-crZvdOd8o2q3VcOSeJvM4YdrNrVaucqExDSqrKMqrU0ISeeTr08YvcbHk6vCKTiyqg7mbK8TsJjeL_JHOHt-eMrvZlBTzDpoFSa6FFYoS3imSMqpKCvBiTWamQxF33JOJaZGZyWlFHEcHcLKDCml6QRc7WLXrX_vTeiKlQva1LVqjO9DQSjDqRQkzSJ6-Q9d-r6NPw4UT2UmEBeRut5RuvUhtMYW69atVLspMCqGxotc5vlP49MIX-wj-3Jlqj_0t2L6Dbe7fN0</recordid><startdate>20200228</startdate><enddate>20200228</enddate><creator>Yang, Zhi-Fang</creator><creator>Xu, Chang</creator><creator>Zheng, Xing</creator><creator>Zhang, Xingang</creator><general>Royal Society of Chemistry</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-4406-6533</orcidid></search><sort><creationdate>20200228</creationdate><title>Nickel-catalyzed carbodifunctionalization of N-vinylamides enables access to γ-amino acids</title><author>Yang, Zhi-Fang ; Xu, Chang ; Zheng, Xing ; Zhang, Xingang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c315t-fa12cb8f8af267a24638bd862fec5e70fa1f663913ec7b333061ec525b70aac3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Amides - chemistry</topic><topic>Amino acids</topic><topic>Amino Acids - chemistry</topic><topic>Carbonyl groups</topic><topic>Carbonyls</topic><topic>Cascade chemical reactions</topic><topic>Catalysis</topic><topic>Chelating Agents - chemistry</topic><topic>Chelation</topic><topic>Esters</topic><topic>Functional groups</topic><topic>Nickel</topic><topic>Nickel - chemistry</topic><topic>Organic chemistry</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yang, Zhi-Fang</creatorcontrib><creatorcontrib>Xu, Chang</creatorcontrib><creatorcontrib>Zheng, Xing</creatorcontrib><creatorcontrib>Zhang, Xingang</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical communications (Cambridge, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yang, Zhi-Fang</au><au>Xu, Chang</au><au>Zheng, Xing</au><au>Zhang, Xingang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Nickel-catalyzed carbodifunctionalization of N-vinylamides enables access to γ-amino acids</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><addtitle>Chem Commun (Camb)</addtitle><date>2020-02-28</date><risdate>2020</risdate><volume>56</volume><issue>17</issue><spage>2642</spage><epage>2645</epage><pages>2642-2645</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>A nickel-catalyzed tandem reaction of N-vinylamides with arylboronic acids and bromodifluoroacetate has been developed. 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| identifier | ISSN: 1359-7345 |
| ispartof | Chemical communications (Cambridge, England), 2020-02, Vol.56 (17), p.2642-2645 |
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| language | eng |
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| source | MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Amides - chemistry Amino acids Amino Acids - chemistry Carbonyl groups Carbonyls Cascade chemical reactions Catalysis Chelating Agents - chemistry Chelation Esters Functional groups Nickel Nickel - chemistry Organic chemistry Substrates |
| title | Nickel-catalyzed carbodifunctionalization of N-vinylamides enables access to γ-amino acids |
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