Copper-Catalyzed Synthesis of [gamma]-Amino Acids Featuring Quaternary Stereocenters
The first general asymmetric synthesis of [gamma],[gamma]-disubstituted [gamma]-amino acids by copper-catalyzed ring opening of nonstrained lactones with amines is reported. This approach features ample scope, operational simplicity, and wide functional-group diversity. The catalytic process allows...
Gespeichert in:
| Veröffentlicht in: | Angewandte Chemie International Edition 2017-11, Vol.56 (47), p.15035 |
|---|---|
| Hauptverfasser: | , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | |
|---|---|
| container_issue | 47 |
| container_start_page | 15035 |
| container_title | Angewandte Chemie International Edition |
| container_volume | 56 |
| creator | Gomez, José Enrique Guo, Wusheng Gaspa, Silvia Kleij, Arjan W |
| description | The first general asymmetric synthesis of [gamma],[gamma]-disubstituted [gamma]-amino acids by copper-catalyzed ring opening of nonstrained lactones with amines is reported. This approach features ample scope, operational simplicity, and wide functional-group diversity. The catalytic process allows access to a series of highly functionalized enantioenriched [gamma]-amino acids featuring quaternary stereocenters with excellent enantiomeric ratios of up to 98:2 and excellent yields of up to 98%. |
| doi_str_mv | 10.1002/anie.201709511 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest</sourceid><recordid>TN_cdi_proquest_journals_1963867801</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1963867801</sourcerecordid><originalsourceid>FETCH-LOGICAL-g150t-94f46b7d3244a19c84730fb56643750a5aa0679f936559605e0452ad49246e9f3</originalsourceid><addsrcrecordid>eNotjktLw0AURgdRsFa3rgdcT73zzixDsFYoiLSuRMptMhNT8jKTLOqvN6CrcxYfh4-Qew4rDiAesa38SgC34DTnF2TBteBMWisvZ1dSMptofk1uYjzN-yQBsyD7rOt7P7AMR6zPP76gu3M7fvlYRdoF-lFi0-AnS5uq7WiaV0Wka4_jNFRtSd8mHP3Q4nCmu1l8l_t2ZrwlVwHr6O_-uSTv66d9tmHb1-eXLN2ykmsYmVNBmaMtpFAKucsTZSWEozZGSasBNSIY64KTRmtnQHtQWmChnFDGuyCX5OGv2w_d9-TjeDh10_ynjgfujEyMTYDLXxlJUa4</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1963867801</pqid></control><display><type>article</type><title>Copper-Catalyzed Synthesis of [gamma]-Amino Acids Featuring Quaternary Stereocenters</title><source>Wiley Online Library Journals Frontfile Complete</source><creator>Gomez, José Enrique ; Guo, Wusheng ; Gaspa, Silvia ; Kleij, Arjan W</creator><creatorcontrib>Gomez, José Enrique ; Guo, Wusheng ; Gaspa, Silvia ; Kleij, Arjan W</creatorcontrib><description>The first general asymmetric synthesis of [gamma],[gamma]-disubstituted [gamma]-amino acids by copper-catalyzed ring opening of nonstrained lactones with amines is reported. This approach features ample scope, operational simplicity, and wide functional-group diversity. The catalytic process allows access to a series of highly functionalized enantioenriched [gamma]-amino acids featuring quaternary stereocenters with excellent enantiomeric ratios of up to 98:2 and excellent yields of up to 98%.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201709511</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Amines ; Amino acids ; Asymmetric synthesis ; Catalysis ; Chemical synthesis ; Copper ; Lactones ; Ring opening</subject><ispartof>Angewandte Chemie International Edition, 2017-11, Vol.56 (47), p.15035</ispartof><rights>2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,777,781,27905,27906</link.rule.ids></links><search><creatorcontrib>Gomez, José Enrique</creatorcontrib><creatorcontrib>Guo, Wusheng</creatorcontrib><creatorcontrib>Gaspa, Silvia</creatorcontrib><creatorcontrib>Kleij, Arjan W</creatorcontrib><title>Copper-Catalyzed Synthesis of [gamma]-Amino Acids Featuring Quaternary Stereocenters</title><title>Angewandte Chemie International Edition</title><description>The first general asymmetric synthesis of [gamma],[gamma]-disubstituted [gamma]-amino acids by copper-catalyzed ring opening of nonstrained lactones with amines is reported. This approach features ample scope, operational simplicity, and wide functional-group diversity. The catalytic process allows access to a series of highly functionalized enantioenriched [gamma]-amino acids featuring quaternary stereocenters with excellent enantiomeric ratios of up to 98:2 and excellent yields of up to 98%.</description><subject>Amines</subject><subject>Amino acids</subject><subject>Asymmetric synthesis</subject><subject>Catalysis</subject><subject>Chemical synthesis</subject><subject>Copper</subject><subject>Lactones</subject><subject>Ring opening</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNotjktLw0AURgdRsFa3rgdcT73zzixDsFYoiLSuRMptMhNT8jKTLOqvN6CrcxYfh4-Qew4rDiAesa38SgC34DTnF2TBteBMWisvZ1dSMptofk1uYjzN-yQBsyD7rOt7P7AMR6zPP76gu3M7fvlYRdoF-lFi0-AnS5uq7WiaV0Wka4_jNFRtSd8mHP3Q4nCmu1l8l_t2ZrwlVwHr6O_-uSTv66d9tmHb1-eXLN2ykmsYmVNBmaMtpFAKucsTZSWEozZGSasBNSIY64KTRmtnQHtQWmChnFDGuyCX5OGv2w_d9-TjeDh10_ynjgfujEyMTYDLXxlJUa4</recordid><startdate>20171120</startdate><enddate>20171120</enddate><creator>Gomez, José Enrique</creator><creator>Guo, Wusheng</creator><creator>Gaspa, Silvia</creator><creator>Kleij, Arjan W</creator><general>Wiley Subscription Services, Inc</general><scope>7TM</scope><scope>K9.</scope></search><sort><creationdate>20171120</creationdate><title>Copper-Catalyzed Synthesis of [gamma]-Amino Acids Featuring Quaternary Stereocenters</title><author>Gomez, José Enrique ; Guo, Wusheng ; Gaspa, Silvia ; Kleij, Arjan W</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-g150t-94f46b7d3244a19c84730fb56643750a5aa0679f936559605e0452ad49246e9f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Amines</topic><topic>Amino acids</topic><topic>Asymmetric synthesis</topic><topic>Catalysis</topic><topic>Chemical synthesis</topic><topic>Copper</topic><topic>Lactones</topic><topic>Ring opening</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gomez, José Enrique</creatorcontrib><creatorcontrib>Guo, Wusheng</creatorcontrib><creatorcontrib>Gaspa, Silvia</creatorcontrib><creatorcontrib>Kleij, Arjan W</creatorcontrib><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Gomez, José Enrique</au><au>Guo, Wusheng</au><au>Gaspa, Silvia</au><au>Kleij, Arjan W</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Copper-Catalyzed Synthesis of [gamma]-Amino Acids Featuring Quaternary Stereocenters</atitle><jtitle>Angewandte Chemie International Edition</jtitle><date>2017-11-20</date><risdate>2017</risdate><volume>56</volume><issue>47</issue><spage>15035</spage><pages>15035-</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>The first general asymmetric synthesis of [gamma],[gamma]-disubstituted [gamma]-amino acids by copper-catalyzed ring opening of nonstrained lactones with amines is reported. This approach features ample scope, operational simplicity, and wide functional-group diversity. The catalytic process allows access to a series of highly functionalized enantioenriched [gamma]-amino acids featuring quaternary stereocenters with excellent enantiomeric ratios of up to 98:2 and excellent yields of up to 98%.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/anie.201709511</doi><edition>International ed. in English</edition></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1433-7851 |
| ispartof | Angewandte Chemie International Edition, 2017-11, Vol.56 (47), p.15035 |
| issn | 1433-7851 1521-3773 |
| language | eng |
| recordid | cdi_proquest_journals_1963867801 |
| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Amines Amino acids Asymmetric synthesis Catalysis Chemical synthesis Copper Lactones Ring opening |
| title | Copper-Catalyzed Synthesis of [gamma]-Amino Acids Featuring Quaternary Stereocenters |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-18T05%3A40%3A35IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Copper-Catalyzed%20Synthesis%20of%20%5Bgamma%5D-Amino%20Acids%20Featuring%20Quaternary%20Stereocenters&rft.jtitle=Angewandte%20Chemie%20International%20Edition&rft.au=Gomez,%20Jos%C3%A9%20Enrique&rft.date=2017-11-20&rft.volume=56&rft.issue=47&rft.spage=15035&rft.pages=15035-&rft.issn=1433-7851&rft.eissn=1521-3773&rft_id=info:doi/10.1002/anie.201709511&rft_dat=%3Cproquest%3E1963867801%3C/proquest%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1963867801&rft_id=info:pmid/&rfr_iscdi=true |