Copper(I) Catalyzed Regioselective Asymmetric Alkoxyamination of Aryl Enamide Derivatives
The copper(I) catalyzed reaction of an enamide with an iminoiodane, in the presence of an alcohol, triggers the direct alkoxyamination of the double bond. This transformation represents a straightforward access to α-amino aminals in a completely regio- and diastereoselective manner. Use of a chiral...
Gespeichert in:
| Veröffentlicht in: | Organic letters 2011-11, Vol.13 (21), p.5792-5795 |
|---|---|
| Hauptverfasser: | , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 5795 |
|---|---|
| container_issue | 21 |
| container_start_page | 5792 |
| container_title | Organic letters |
| container_volume | 13 |
| creator | Nakanishi, Masafumi Minard, Corinne Retailleau, Pascal Cariou, Kevin Dodd, Robert H |
| description | The copper(I) catalyzed reaction of an enamide with an iminoiodane, in the presence of an alcohol, triggers the direct alkoxyamination of the double bond. This transformation represents a straightforward access to α-amino aminals in a completely regio- and diastereoselective manner. Use of a chiral Box ligand allows this reaction to be carried out in an enantioselective fashion. |
| doi_str_mv | 10.1021/ol202367d |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_hal_p</sourceid><recordid>TN_cdi_hal_primary_oai_HAL_hal_00647697v1</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>901006656</sourcerecordid><originalsourceid>FETCH-LOGICAL-a449t-52a564d477208ddf5d56d4f6129a63d2bae6da11790835d3c3b30298e777cd473</originalsourceid><addsrcrecordid>eNptkD1PwzAURS0EoqUw8AdQFgQdCv5I7GaMSqGVKiEhGJgsN34BFycudloRfj2pWsrC9J6uzj3DReic4BuCKbl1lmLKuNAHqEsSygYCJ_Rw_3PcQSchLDAmbZIeow4lqWBE8C56HbnlEvz1tB-NVK1s8w06eoI34wJYyGuzhigLTVlC7U0eZfbDfTWqNJWqjasiV0SZb2w0rtpMQ3QH3qzVphVO0VGhbICz3e2hl_vx82gymD0-TEfZbKDiOK0HCVUJj3UsBMVDrYtEJ1zHBSc0VZxpOlfAtSJEpHjIEs1yNmeYpkMQQuRtjfVQf-t9V1YuvSmVb6RTRk6ymdxkGPNY8FSsSctebdmld58rCLUsTcjBWlWBWwWZYtLSPOF_1ty7EDwUezXBcjO63I_eshc762pegt6Tvyu3wOUWUHmQC7fyVTvIP6IfHOaHNQ</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>901006656</pqid></control><display><type>article</type><title>Copper(I) Catalyzed Regioselective Asymmetric Alkoxyamination of Aryl Enamide Derivatives</title><source>MEDLINE</source><source>ACS Publications</source><creator>Nakanishi, Masafumi ; Minard, Corinne ; Retailleau, Pascal ; Cariou, Kevin ; Dodd, Robert H</creator><creatorcontrib>Nakanishi, Masafumi ; Minard, Corinne ; Retailleau, Pascal ; Cariou, Kevin ; Dodd, Robert H</creatorcontrib><description>The copper(I) catalyzed reaction of an enamide with an iminoiodane, in the presence of an alcohol, triggers the direct alkoxyamination of the double bond. This transformation represents a straightforward access to α-amino aminals in a completely regio- and diastereoselective manner. Use of a chiral Box ligand allows this reaction to be carried out in an enantioselective fashion.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol202367d</identifier><identifier>PMID: 21973176</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Alcohols - chemistry ; Amides - chemistry ; Amination ; Catalysis ; Chemical Sciences ; Copper - chemistry ; Ligands ; Molecular Structure ; Organic chemistry ; Stereoisomerism</subject><ispartof>Organic letters, 2011-11, Vol.13 (21), p.5792-5795</ispartof><rights>Copyright © 2011 American Chemical Society</rights><rights>2011 American Chemical Society</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a449t-52a564d477208ddf5d56d4f6129a63d2bae6da11790835d3c3b30298e777cd473</citedby><cites>FETCH-LOGICAL-a449t-52a564d477208ddf5d56d4f6129a63d2bae6da11790835d3c3b30298e777cd473</cites><orcidid>0000-0003-3995-519X ; 0000-0002-5854-9632</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ol202367d$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol202367d$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>230,314,780,784,885,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21973176$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-00647697$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Nakanishi, Masafumi</creatorcontrib><creatorcontrib>Minard, Corinne</creatorcontrib><creatorcontrib>Retailleau, Pascal</creatorcontrib><creatorcontrib>Cariou, Kevin</creatorcontrib><creatorcontrib>Dodd, Robert H</creatorcontrib><title>Copper(I) Catalyzed Regioselective Asymmetric Alkoxyamination of Aryl Enamide Derivatives</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>The copper(I) catalyzed reaction of an enamide with an iminoiodane, in the presence of an alcohol, triggers the direct alkoxyamination of the double bond. This transformation represents a straightforward access to α-amino aminals in a completely regio- and diastereoselective manner. Use of a chiral Box ligand allows this reaction to be carried out in an enantioselective fashion.</description><subject>Alcohols - chemistry</subject><subject>Amides - chemistry</subject><subject>Amination</subject><subject>Catalysis</subject><subject>Chemical Sciences</subject><subject>Copper - chemistry</subject><subject>Ligands</subject><subject>Molecular Structure</subject><subject>Organic chemistry</subject><subject>Stereoisomerism</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkD1PwzAURS0EoqUw8AdQFgQdCv5I7GaMSqGVKiEhGJgsN34BFycudloRfj2pWsrC9J6uzj3DReic4BuCKbl1lmLKuNAHqEsSygYCJ_Rw_3PcQSchLDAmbZIeow4lqWBE8C56HbnlEvz1tB-NVK1s8w06eoI34wJYyGuzhigLTVlC7U0eZfbDfTWqNJWqjasiV0SZb2w0rtpMQ3QH3qzVphVO0VGhbICz3e2hl_vx82gymD0-TEfZbKDiOK0HCVUJj3UsBMVDrYtEJ1zHBSc0VZxpOlfAtSJEpHjIEs1yNmeYpkMQQuRtjfVQf-t9V1YuvSmVb6RTRk6ymdxkGPNY8FSsSctebdmld58rCLUsTcjBWlWBWwWZYtLSPOF_1ty7EDwUezXBcjO63I_eshc762pegt6Tvyu3wOUWUHmQC7fyVTvIP6IfHOaHNQ</recordid><startdate>20111104</startdate><enddate>20111104</enddate><creator>Nakanishi, Masafumi</creator><creator>Minard, Corinne</creator><creator>Retailleau, Pascal</creator><creator>Cariou, Kevin</creator><creator>Dodd, Robert H</creator><general>American Chemical Society</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>7X8</scope><scope>1XC</scope><scope>VOOES</scope><orcidid>https://orcid.org/0000-0003-3995-519X</orcidid><orcidid>https://orcid.org/0000-0002-5854-9632</orcidid></search><sort><creationdate>20111104</creationdate><title>Copper(I) Catalyzed Regioselective Asymmetric Alkoxyamination of Aryl Enamide Derivatives</title><author>Nakanishi, Masafumi ; Minard, Corinne ; Retailleau, Pascal ; Cariou, Kevin ; Dodd, Robert H</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a449t-52a564d477208ddf5d56d4f6129a63d2bae6da11790835d3c3b30298e777cd473</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Alcohols - chemistry</topic><topic>Amides - chemistry</topic><topic>Amination</topic><topic>Catalysis</topic><topic>Chemical Sciences</topic><topic>Copper - chemistry</topic><topic>Ligands</topic><topic>Molecular Structure</topic><topic>Organic chemistry</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nakanishi, Masafumi</creatorcontrib><creatorcontrib>Minard, Corinne</creatorcontrib><creatorcontrib>Retailleau, Pascal</creatorcontrib><creatorcontrib>Cariou, Kevin</creatorcontrib><creatorcontrib>Dodd, Robert H</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>Hyper Article en Ligne (HAL)</collection><collection>Hyper Article en Ligne (HAL) (Open Access)</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Nakanishi, Masafumi</au><au>Minard, Corinne</au><au>Retailleau, Pascal</au><au>Cariou, Kevin</au><au>Dodd, Robert H</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Copper(I) Catalyzed Regioselective Asymmetric Alkoxyamination of Aryl Enamide Derivatives</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2011-11-04</date><risdate>2011</risdate><volume>13</volume><issue>21</issue><spage>5792</spage><epage>5795</epage><pages>5792-5795</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>The copper(I) catalyzed reaction of an enamide with an iminoiodane, in the presence of an alcohol, triggers the direct alkoxyamination of the double bond. This transformation represents a straightforward access to α-amino aminals in a completely regio- and diastereoselective manner. Use of a chiral Box ligand allows this reaction to be carried out in an enantioselective fashion.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>21973176</pmid><doi>10.1021/ol202367d</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0003-3995-519X</orcidid><orcidid>https://orcid.org/0000-0002-5854-9632</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2011-11, Vol.13 (21), p.5792-5795 |
| issn | 1523-7060 1523-7052 |
| language | eng |
| recordid | cdi_hal_primary_oai_HAL_hal_00647697v1 |
| source | MEDLINE; ACS Publications |
| subjects | Alcohols - chemistry Amides - chemistry Amination Catalysis Chemical Sciences Copper - chemistry Ligands Molecular Structure Organic chemistry Stereoisomerism |
| title | Copper(I) Catalyzed Regioselective Asymmetric Alkoxyamination of Aryl Enamide Derivatives |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-23T00%3A59%3A17IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_hal_p&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Copper(I)%20Catalyzed%20Regioselective%20Asymmetric%20Alkoxyamination%20of%20Aryl%20Enamide%20Derivatives&rft.jtitle=Organic%20letters&rft.au=Nakanishi,%20Masafumi&rft.date=2011-11-04&rft.volume=13&rft.issue=21&rft.spage=5792&rft.epage=5795&rft.pages=5792-5795&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/ol202367d&rft_dat=%3Cproquest_hal_p%3E901006656%3C/proquest_hal_p%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=901006656&rft_id=info:pmid/21973176&rfr_iscdi=true |