Preparation of Tertiary Amines by the Reaction of Iminium Ions Derived from Unsymmetrical Aminals with Zinc and Magnesium Organometallics

Preparation of Tertiary Amines by the Reaction of Iminium Ions Derived from Unsymmetrical Aminals with Zinc and Magnesium Organometallics

We report a convenient one-pot preparation of polyfunctional tertiary amines, including various biorelevant phenethylamines or ephedrine derivatives, via the reaction of new functionalized iminium ions with a variety of zinc and magnesium organometallic reagents. These iminium ions were generated fr...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2015-04, Vol.17 (8), p.2026-2029
Hauptverfasser: Werner, Veronika, Ellwart, Mario, Wagner, Andreas J, Knochel, Paul
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 2029
container_issue 8
container_start_page 2026
container_title Organic letters
container_volume 17
creator Werner, Veronika
Ellwart, Mario
Wagner, Andreas J
Knochel, Paul
description We report a convenient one-pot preparation of polyfunctional tertiary amines, including various biorelevant phenethylamines or ephedrine derivatives, via the reaction of new functionalized iminium ions with a variety of zinc and magnesium organometallic reagents. These iminium ions were generated from unsymmetrical aminals, obtained by the in situ addition of various amides to Tietze’s iminium salt [Me2NCH2 +CF3COO–]. A functionalized aniline, prepared by this method, was converted to a quinolidine via an intramolecular Heck reaction.
doi_str_mv 10.1021/acs.orglett.5b00801
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1674205537</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1674205537</sourcerecordid><originalsourceid>FETCH-LOGICAL-a345t-25e650f7dcd80c3b366d16bf7bddf19cf61e96d598d5b2c5cc4cbae7028e9ee83</originalsourceid><addsrcrecordid>eNp9kUtPAjEUhRujEUR_gYnp0s1AO0PnsST4IsFgDGzcTDrtHSiZmWLb0fAT_NcWeSxd3eb2O-cm5yB0S0mfkpAOuLB9bZYVONdnBSEpoWeoS1kYBQlh4fnpHZMOurJ2TQj1m-wSdUKWDjOWJF3082Zgww13SjdYl3gOxilutnhUqwYsLrbYrQC_AxdHZOJ_VFvjiW4sfgCjvkDi0ugaLxq7rWtwRgle_TnwyuJv5Vb4QzUC80biV770vjv9zCx5oz3Oq0oJe40uSo_DzWH20OLpcT5-Caaz58l4NA14NGQuCBnEjJSJFDIlIiqiOJY0LsqkkLKkmShjClksWZZKVoSCCTEUBYeEhClkAGnUQ_d7343Rny1Yl9fKCqgq3oBubU7jZBgSxqLEo9EeFUZba6DMN0bVPp2cknzXQe47yA8d5IcOvOrucKAtapAnzTF0Dwz2wE691q3ZxfSv5S8pRJk6</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1674205537</pqid></control><display><type>article</type><title>Preparation of Tertiary Amines by the Reaction of Iminium Ions Derived from Unsymmetrical Aminals with Zinc and Magnesium Organometallics</title><source>American Chemical Society Journals</source><creator>Werner, Veronika ; Ellwart, Mario ; Wagner, Andreas J ; Knochel, Paul</creator><creatorcontrib>Werner, Veronika ; Ellwart, Mario ; Wagner, Andreas J ; Knochel, Paul</creatorcontrib><description>We report a convenient one-pot preparation of polyfunctional tertiary amines, including various biorelevant phenethylamines or ephedrine derivatives, via the reaction of new functionalized iminium ions with a variety of zinc and magnesium organometallic reagents. These iminium ions were generated from unsymmetrical aminals, obtained by the in situ addition of various amides to Tietze’s iminium salt [Me2NCH2 +CF3COO–]. A functionalized aniline, prepared by this method, was converted to a quinolidine via an intramolecular Heck reaction.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.5b00801</identifier><identifier>PMID: 25849577</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Organic letters, 2015-04, Vol.17 (8), p.2026-2029</ispartof><rights>Copyright © American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a345t-25e650f7dcd80c3b366d16bf7bddf19cf61e96d598d5b2c5cc4cbae7028e9ee83</citedby><cites>FETCH-LOGICAL-a345t-25e650f7dcd80c3b366d16bf7bddf19cf61e96d598d5b2c5cc4cbae7028e9ee83</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.orglett.5b00801$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.orglett.5b00801$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2751,27055,27903,27904,56717,56767</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25849577$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Werner, Veronika</creatorcontrib><creatorcontrib>Ellwart, Mario</creatorcontrib><creatorcontrib>Wagner, Andreas J</creatorcontrib><creatorcontrib>Knochel, Paul</creatorcontrib><title>Preparation of Tertiary Amines by the Reaction of Iminium Ions Derived from Unsymmetrical Aminals with Zinc and Magnesium Organometallics</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>We report a convenient one-pot preparation of polyfunctional tertiary amines, including various biorelevant phenethylamines or ephedrine derivatives, via the reaction of new functionalized iminium ions with a variety of zinc and magnesium organometallic reagents. These iminium ions were generated from unsymmetrical aminals, obtained by the in situ addition of various amides to Tietze’s iminium salt [Me2NCH2 +CF3COO–]. A functionalized aniline, prepared by this method, was converted to a quinolidine via an intramolecular Heck reaction.</description><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNp9kUtPAjEUhRujEUR_gYnp0s1AO0PnsST4IsFgDGzcTDrtHSiZmWLb0fAT_NcWeSxd3eb2O-cm5yB0S0mfkpAOuLB9bZYVONdnBSEpoWeoS1kYBQlh4fnpHZMOurJ2TQj1m-wSdUKWDjOWJF3082Zgww13SjdYl3gOxilutnhUqwYsLrbYrQC_AxdHZOJ_VFvjiW4sfgCjvkDi0ugaLxq7rWtwRgle_TnwyuJv5Vb4QzUC80biV770vjv9zCx5oz3Oq0oJe40uSo_DzWH20OLpcT5-Caaz58l4NA14NGQuCBnEjJSJFDIlIiqiOJY0LsqkkLKkmShjClksWZZKVoSCCTEUBYeEhClkAGnUQ_d7343Rny1Yl9fKCqgq3oBubU7jZBgSxqLEo9EeFUZba6DMN0bVPp2cknzXQe47yA8d5IcOvOrucKAtapAnzTF0Dwz2wE691q3ZxfSv5S8pRJk6</recordid><startdate>20150417</startdate><enddate>20150417</enddate><creator>Werner, Veronika</creator><creator>Ellwart, Mario</creator><creator>Wagner, Andreas J</creator><creator>Knochel, Paul</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20150417</creationdate><title>Preparation of Tertiary Amines by the Reaction of Iminium Ions Derived from Unsymmetrical Aminals with Zinc and Magnesium Organometallics</title><author>Werner, Veronika ; Ellwart, Mario ; Wagner, Andreas J ; Knochel, Paul</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a345t-25e650f7dcd80c3b366d16bf7bddf19cf61e96d598d5b2c5cc4cbae7028e9ee83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Werner, Veronika</creatorcontrib><creatorcontrib>Ellwart, Mario</creatorcontrib><creatorcontrib>Wagner, Andreas J</creatorcontrib><creatorcontrib>Knochel, Paul</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Werner, Veronika</au><au>Ellwart, Mario</au><au>Wagner, Andreas J</au><au>Knochel, Paul</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Preparation of Tertiary Amines by the Reaction of Iminium Ions Derived from Unsymmetrical Aminals with Zinc and Magnesium Organometallics</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2015-04-17</date><risdate>2015</risdate><volume>17</volume><issue>8</issue><spage>2026</spage><epage>2029</epage><pages>2026-2029</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>We report a convenient one-pot preparation of polyfunctional tertiary amines, including various biorelevant phenethylamines or ephedrine derivatives, via the reaction of new functionalized iminium ions with a variety of zinc and magnesium organometallic reagents. These iminium ions were generated from unsymmetrical aminals, obtained by the in situ addition of various amides to Tietze’s iminium salt [Me2NCH2 +CF3COO–]. A functionalized aniline, prepared by this method, was converted to a quinolidine via an intramolecular Heck reaction.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>25849577</pmid><doi>10.1021/acs.orglett.5b00801</doi><tpages>4</tpages></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2015-04, Vol.17 (8), p.2026-2029
issn 1523-7060
1523-7052
language eng
recordid cdi_proquest_miscellaneous_1674205537
source American Chemical Society Journals
title Preparation of Tertiary Amines by the Reaction of Iminium Ions Derived from Unsymmetrical Aminals with Zinc and Magnesium Organometallics
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-22T18%3A10%3A10IST&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=Preparation%20of%20Tertiary%20Amines%20by%20the%20Reaction%20of%20Iminium%20Ions%20Derived%20from%20Unsymmetrical%20Aminals%20with%20Zinc%20and%20Magnesium%20Organometallics&rft.jtitle=Organic%20letters&rft.au=Werner,%20Veronika&rft.date=2015-04-17&rft.volume=17&rft.issue=8&rft.spage=2026&rft.epage=2029&rft.pages=2026-2029&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/acs.orglett.5b00801&rft_dat=%3Cproquest_cross%3E1674205537%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=1674205537&rft_id=info:pmid/25849577&rfr_iscdi=true