Enantioselective synthesis of arylglycine derivatives by direct C-H oxidative cross-coupling

A new method for the synthesis of chiral α-amino acid derivatives by enantioselective C-H arylation of N-aryl glycine esters with aryl boric acids in the presence of a chiral Pd(II)-catalyst has been developed. This work successfully integrates the direct C-H oxidation with asymmetric arylation and...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Chemical communications (Cambridge, England) England), 2015-01, Vol.51 (5), p.832-835
Hauptverfasser: Wei, Xiao-Hong, Wang, Gang-Wei, Yang, Shang-Dong
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 835
container_issue 5
container_start_page 832
container_title Chemical communications (Cambridge, England)
container_volume 51
creator Wei, Xiao-Hong
Wang, Gang-Wei
Yang, Shang-Dong
description A new method for the synthesis of chiral α-amino acid derivatives by enantioselective C-H arylation of N-aryl glycine esters with aryl boric acids in the presence of a chiral Pd(II)-catalyst has been developed. This work successfully integrates the direct C-H oxidation with asymmetric arylation and exhibits excellent enantioselectivity.
doi_str_mv 10.1039/c4cc07361d
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1893898877</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1893898877</sourcerecordid><originalsourceid>FETCH-LOGICAL-c386t-d48f55b8737683e58ffa82c6477bf93940c4edaa225df3d520d12eae74d07af3</originalsourceid><addsrcrecordid>eNqFkE1LxDAQhoMorq5e_AGSowjVpEma5Ch1dYUFL3vwIJQ0mayRbrs23cX-e7sfenUuMzDPvDAPQleU3FHC9L3l1hLJMuqO0BllGU8EV2_H21noRDIuRug8xk8yFBXqFI1SwbhiXJ6h90lt6i40ESqwXdgAjn3dfUAMETcem7avFlVvQw3YQRs2ZstEXPbYhXa4wHkyxc13cLsFtm0TY2Kb9aoK9eICnXhTRbg89DGaP03m-TSZvT6_5A-zxDKVdYnjygtRKslkphgI5b1Rqc24lKXXTHNiOThj0lQ4z5xIiaMpGJDcEWk8G6Obfeyqbb7WELtiGaKFqjI1NOtYUKWZ0kpJ-T-aMam1SqkY0Ns9uvupBV-s2rAchBSUFFvvRc7zfOf9cYCvD7nrcgnuD_0VzX4AhpF-7A</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1637998215</pqid></control><display><type>article</type><title>Enantioselective synthesis of arylglycine derivatives by direct C-H oxidative cross-coupling</title><source>MEDLINE</source><source>Royal Society Of Chemistry Journals 2008-</source><source>Alma/SFX Local Collection</source><creator>Wei, Xiao-Hong ; Wang, Gang-Wei ; Yang, Shang-Dong</creator><creatorcontrib>Wei, Xiao-Hong ; Wang, Gang-Wei ; Yang, Shang-Dong</creatorcontrib><description>A new method for the synthesis of chiral α-amino acid derivatives by enantioselective C-H arylation of N-aryl glycine esters with aryl boric acids in the presence of a chiral Pd(II)-catalyst has been developed. This work successfully integrates the direct C-H oxidation with asymmetric arylation and exhibits excellent enantioselectivity.</description><identifier>ISSN: 1359-7345</identifier><identifier>EISSN: 1364-548X</identifier><identifier>DOI: 10.1039/c4cc07361d</identifier><identifier>PMID: 25348347</identifier><language>eng</language><publisher>England</publisher><subject>Aromatic compounds ; Asymmetry ; Boric acids ; Carbon - chemistry ; Chemistry Techniques, Synthetic ; Cross coupling ; Derivatives ; Esters ; Glycine ; Glycine - analogs &amp; derivatives ; Glycine - chemical synthesis ; Glycine - chemistry ; Hydrogen - chemistry ; Oxidation-Reduction ; Stereoisomerism ; Substrate Specificity ; Synthesis</subject><ispartof>Chemical communications (Cambridge, England), 2015-01, Vol.51 (5), p.832-835</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c386t-d48f55b8737683e58ffa82c6477bf93940c4edaa225df3d520d12eae74d07af3</citedby><cites>FETCH-LOGICAL-c386t-d48f55b8737683e58ffa82c6477bf93940c4edaa225df3d520d12eae74d07af3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25348347$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wei, Xiao-Hong</creatorcontrib><creatorcontrib>Wang, Gang-Wei</creatorcontrib><creatorcontrib>Yang, Shang-Dong</creatorcontrib><title>Enantioselective synthesis of arylglycine derivatives by direct C-H oxidative cross-coupling</title><title>Chemical communications (Cambridge, England)</title><addtitle>Chem Commun (Camb)</addtitle><description>A new method for the synthesis of chiral α-amino acid derivatives by enantioselective C-H arylation of N-aryl glycine esters with aryl boric acids in the presence of a chiral Pd(II)-catalyst has been developed. This work successfully integrates the direct C-H oxidation with asymmetric arylation and exhibits excellent enantioselectivity.</description><subject>Aromatic compounds</subject><subject>Asymmetry</subject><subject>Boric acids</subject><subject>Carbon - chemistry</subject><subject>Chemistry Techniques, Synthetic</subject><subject>Cross coupling</subject><subject>Derivatives</subject><subject>Esters</subject><subject>Glycine</subject><subject>Glycine - analogs &amp; derivatives</subject><subject>Glycine - chemical synthesis</subject><subject>Glycine - chemistry</subject><subject>Hydrogen - chemistry</subject><subject>Oxidation-Reduction</subject><subject>Stereoisomerism</subject><subject>Substrate Specificity</subject><subject>Synthesis</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkE1LxDAQhoMorq5e_AGSowjVpEma5Ch1dYUFL3vwIJQ0mayRbrs23cX-e7sfenUuMzDPvDAPQleU3FHC9L3l1hLJMuqO0BllGU8EV2_H21noRDIuRug8xk8yFBXqFI1SwbhiXJ6h90lt6i40ESqwXdgAjn3dfUAMETcem7avFlVvQw3YQRs2ZstEXPbYhXa4wHkyxc13cLsFtm0TY2Kb9aoK9eICnXhTRbg89DGaP03m-TSZvT6_5A-zxDKVdYnjygtRKslkphgI5b1Rqc24lKXXTHNiOThj0lQ4z5xIiaMpGJDcEWk8G6Obfeyqbb7WELtiGaKFqjI1NOtYUKWZ0kpJ-T-aMam1SqkY0Ns9uvupBV-s2rAchBSUFFvvRc7zfOf9cYCvD7nrcgnuD_0VzX4AhpF-7A</recordid><startdate>20150118</startdate><enddate>20150118</enddate><creator>Wei, Xiao-Hong</creator><creator>Wang, Gang-Wei</creator><creator>Yang, Shang-Dong</creator><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>7X8</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20150118</creationdate><title>Enantioselective synthesis of arylglycine derivatives by direct C-H oxidative cross-coupling</title><author>Wei, Xiao-Hong ; Wang, Gang-Wei ; Yang, Shang-Dong</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c386t-d48f55b8737683e58ffa82c6477bf93940c4edaa225df3d520d12eae74d07af3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Aromatic compounds</topic><topic>Asymmetry</topic><topic>Boric acids</topic><topic>Carbon - chemistry</topic><topic>Chemistry Techniques, Synthetic</topic><topic>Cross coupling</topic><topic>Derivatives</topic><topic>Esters</topic><topic>Glycine</topic><topic>Glycine - analogs &amp; derivatives</topic><topic>Glycine - chemical synthesis</topic><topic>Glycine - chemistry</topic><topic>Hydrogen - chemistry</topic><topic>Oxidation-Reduction</topic><topic>Stereoisomerism</topic><topic>Substrate Specificity</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wei, Xiao-Hong</creatorcontrib><creatorcontrib>Wang, Gang-Wei</creatorcontrib><creatorcontrib>Yang, Shang-Dong</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</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><jtitle>Chemical communications (Cambridge, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wei, Xiao-Hong</au><au>Wang, Gang-Wei</au><au>Yang, Shang-Dong</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enantioselective synthesis of arylglycine derivatives by direct C-H oxidative cross-coupling</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><addtitle>Chem Commun (Camb)</addtitle><date>2015-01-18</date><risdate>2015</risdate><volume>51</volume><issue>5</issue><spage>832</spage><epage>835</epage><pages>832-835</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>A new method for the synthesis of chiral α-amino acid derivatives by enantioselective C-H arylation of N-aryl glycine esters with aryl boric acids in the presence of a chiral Pd(II)-catalyst has been developed. This work successfully integrates the direct C-H oxidation with asymmetric arylation and exhibits excellent enantioselectivity.</abstract><cop>England</cop><pmid>25348347</pmid><doi>10.1039/c4cc07361d</doi><tpages>4</tpages></addata></record>
fulltext fulltext
identifier ISSN: 1359-7345
ispartof Chemical communications (Cambridge, England), 2015-01, Vol.51 (5), p.832-835
issn 1359-7345
1364-548X
language eng
recordid cdi_proquest_miscellaneous_1893898877
source MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection
subjects Aromatic compounds
Asymmetry
Boric acids
Carbon - chemistry
Chemistry Techniques, Synthetic
Cross coupling
Derivatives
Esters
Glycine
Glycine - analogs & derivatives
Glycine - chemical synthesis
Glycine - chemistry
Hydrogen - chemistry
Oxidation-Reduction
Stereoisomerism
Substrate Specificity
Synthesis
title Enantioselective synthesis of arylglycine derivatives by direct C-H oxidative cross-coupling
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-02T10%3A00%3A59IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Enantioselective%20synthesis%20of%20arylglycine%20derivatives%20by%20direct%20C-H%20oxidative%20cross-coupling&rft.jtitle=Chemical%20communications%20(Cambridge,%20England)&rft.au=Wei,%20Xiao-Hong&rft.date=2015-01-18&rft.volume=51&rft.issue=5&rft.spage=832&rft.epage=835&rft.pages=832-835&rft.issn=1359-7345&rft.eissn=1364-548X&rft_id=info:doi/10.1039/c4cc07361d&rft_dat=%3Cproquest_cross%3E1893898877%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1637998215&rft_id=info:pmid/25348347&rfr_iscdi=true