A hydrogen borrowing annulation strategy for the stereocontrolled synthesis of saturated aza-heterocycles
An iridium catalyzed method for the synthesis of saturated aza-heterocycles from amines and diols is reported. A wide range of substituted heterocycles can be obtained using this approach including products bearing substituents at the C2, C3 and C4 positions. Employing water as the solvent, enantiop...
Gespeichert in:
| Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2020-03, Vol.56 (24), p.3563-3566 |
|---|---|
| Hauptverfasser: | , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 3566 |
|---|---|
| container_issue | 24 |
| container_start_page | 3563 |
| container_title | Chemical communications (Cambridge, England) |
| container_volume | 56 |
| creator | Chamberlain, Anna E. R. Paterson, Kieran J. Armstrong, Roly J. Twin, Heather C. Donohoe, Timothy J. |
| description | An iridium catalyzed method for the synthesis of saturated aza-heterocycles from amines and diols is reported. A wide range of substituted heterocycles can be obtained using this approach including products bearing substituents at the C2, C3 and C4 positions. Employing water as the solvent, enantiopure diols could undergo annulation with minimal racemization, enabling the synthesis of valuable enantioenriched C3 and C4-substituted saturated aza-heterocycles. |
| doi_str_mv | 10.1039/d0cc00903b |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2366636505</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2382049767</sourcerecordid><originalsourceid>FETCH-LOGICAL-c315t-b18a0bb8c619025462961ea1970f47ae33f8318e799cbda7c2c4b86ee9a32faf3</originalsourceid><addsrcrecordid>eNqN0U1rFTEUBuAgiq3VjT9AAm5EGU0mH5Ms6_hRoeBGwd2QZE7unTI3qUmGMv765t5bu-iq2SQcnnM45EXoNSUfKWH600icI0QTZp-gU8okbwRXf57u30I3HePiBL3I-YrUQ4V6jk5YSwlXXJyi6Rxv1zHFDQRsY0rxZgobbEJYZlOmGHAuyRTYrNjHhMsWagESRBdDSXGeYcR5DbWep4yjx9mUZd8wYvPPNFuoOLrVzZBfomfezBle3d1n6Pe3r7_6i-by5_cf_fll4xgVpbFUGWKtcpJq0gouWy0pGKo74nlngDGvGFXQae3saDrXOm6VBNCGtd54dobeHedep_h3gVyG3ZQdzLMJEJc8tExKyaQgotK3D-hVXFKo21WlWsJ1J7uq3h-VSzHnBH64TtPOpHWgZNgHMHwhfX8I4HPFb-5GLnYH4z39_-MVqCO4ARt9dhMEB_esJiRaqaU6ZKX6qRxS6OMSSm398PhWdguuOqL_</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2382049767</pqid></control><display><type>article</type><title>A hydrogen borrowing annulation strategy for the stereocontrolled synthesis of saturated aza-heterocycles</title><source>Royal Society Of Chemistry Journals 2008-</source><source>Alma/SFX Local Collection</source><creator>Chamberlain, Anna E. R. ; Paterson, Kieran J. ; Armstrong, Roly J. ; Twin, Heather C. ; Donohoe, Timothy J.</creator><creatorcontrib>Chamberlain, Anna E. R. ; Paterson, Kieran J. ; Armstrong, Roly J. ; Twin, Heather C. ; Donohoe, Timothy J.</creatorcontrib><description>An iridium catalyzed method for the synthesis of saturated aza-heterocycles from amines and diols is reported. A wide range of substituted heterocycles can be obtained using this approach including products bearing substituents at the C2, C3 and C4 positions. Employing water as the solvent, enantiopure diols could undergo annulation with minimal racemization, enabling the synthesis of valuable enantioenriched C3 and C4-substituted saturated aza-heterocycles.</description><identifier>ISSN: 1359-7345</identifier><identifier>EISSN: 1364-548X</identifier><identifier>DOI: 10.1039/d0cc00903b</identifier><identifier>PMID: 32104845</identifier><language>eng</language><publisher>CAMBRIDGE: Royal Soc Chemistry</publisher><subject>Amines ; Chemical reactions ; Chemical synthesis ; Chemistry ; Chemistry, Multidisciplinary ; Diols ; Iridium ; Organic chemistry ; Physical Sciences ; Racemization ; Science & Technology ; Substitutes</subject><ispartof>Chemical communications (Cambridge, England), 2020-03, Vol.56 (24), p.3563-3566</ispartof><rights>Copyright Royal Society of Chemistry 2020</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>true</woscitedreferencessubscribed><woscitedreferencescount>25</woscitedreferencescount><woscitedreferencesoriginalsourcerecordid>wos000526968000018</woscitedreferencesoriginalsourcerecordid><citedby>FETCH-LOGICAL-c315t-b18a0bb8c619025462961ea1970f47ae33f8318e799cbda7c2c4b86ee9a32faf3</citedby><cites>FETCH-LOGICAL-c315t-b18a0bb8c619025462961ea1970f47ae33f8318e799cbda7c2c4b86ee9a32faf3</cites><orcidid>0000-0001-7088-6626 ; 0000-0002-3759-061X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,778,782,27911,27912</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/32104845$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Chamberlain, Anna E. R.</creatorcontrib><creatorcontrib>Paterson, Kieran J.</creatorcontrib><creatorcontrib>Armstrong, Roly J.</creatorcontrib><creatorcontrib>Twin, Heather C.</creatorcontrib><creatorcontrib>Donohoe, Timothy J.</creatorcontrib><title>A hydrogen borrowing annulation strategy for the stereocontrolled synthesis of saturated aza-heterocycles</title><title>Chemical communications (Cambridge, England)</title><addtitle>CHEM COMMUN</addtitle><addtitle>Chem Commun (Camb)</addtitle><description>An iridium catalyzed method for the synthesis of saturated aza-heterocycles from amines and diols is reported. A wide range of substituted heterocycles can be obtained using this approach including products bearing substituents at the C2, C3 and C4 positions. Employing water as the solvent, enantiopure diols could undergo annulation with minimal racemization, enabling the synthesis of valuable enantioenriched C3 and C4-substituted saturated aza-heterocycles.</description><subject>Amines</subject><subject>Chemical reactions</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Chemistry, Multidisciplinary</subject><subject>Diols</subject><subject>Iridium</subject><subject>Organic chemistry</subject><subject>Physical Sciences</subject><subject>Racemization</subject><subject>Science & Technology</subject><subject>Substitutes</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>AOWDO</sourceid><recordid>eNqN0U1rFTEUBuAgiq3VjT9AAm5EGU0mH5Ms6_hRoeBGwd2QZE7unTI3qUmGMv765t5bu-iq2SQcnnM45EXoNSUfKWH600icI0QTZp-gU8okbwRXf57u30I3HePiBL3I-YrUQ4V6jk5YSwlXXJyi6Rxv1zHFDQRsY0rxZgobbEJYZlOmGHAuyRTYrNjHhMsWagESRBdDSXGeYcR5DbWep4yjx9mUZd8wYvPPNFuoOLrVzZBfomfezBle3d1n6Pe3r7_6i-by5_cf_fll4xgVpbFUGWKtcpJq0gouWy0pGKo74nlngDGvGFXQae3saDrXOm6VBNCGtd54dobeHedep_h3gVyG3ZQdzLMJEJc8tExKyaQgotK3D-hVXFKo21WlWsJ1J7uq3h-VSzHnBH64TtPOpHWgZNgHMHwhfX8I4HPFb-5GLnYH4z39_-MVqCO4ARt9dhMEB_esJiRaqaU6ZKX6qRxS6OMSSm398PhWdguuOqL_</recordid><startdate>20200325</startdate><enddate>20200325</enddate><creator>Chamberlain, Anna E. R.</creator><creator>Paterson, Kieran J.</creator><creator>Armstrong, Roly J.</creator><creator>Twin, Heather C.</creator><creator>Donohoe, Timothy J.</creator><general>Royal Soc Chemistry</general><general>Royal Society of Chemistry</general><scope>1KM</scope><scope>1KN</scope><scope>AOWDO</scope><scope>BLEPL</scope><scope>DTL</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/0000-0001-7088-6626</orcidid><orcidid>https://orcid.org/0000-0002-3759-061X</orcidid></search><sort><creationdate>20200325</creationdate><title>A hydrogen borrowing annulation strategy for the stereocontrolled synthesis of saturated aza-heterocycles</title><author>Chamberlain, Anna E. R. ; Paterson, Kieran J. ; Armstrong, Roly J. ; Twin, Heather C. ; Donohoe, Timothy J.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c315t-b18a0bb8c619025462961ea1970f47ae33f8318e799cbda7c2c4b86ee9a32faf3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Amines</topic><topic>Chemical reactions</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Chemistry, Multidisciplinary</topic><topic>Diols</topic><topic>Iridium</topic><topic>Organic chemistry</topic><topic>Physical Sciences</topic><topic>Racemization</topic><topic>Science & Technology</topic><topic>Substitutes</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chamberlain, Anna E. R.</creatorcontrib><creatorcontrib>Paterson, Kieran J.</creatorcontrib><creatorcontrib>Armstrong, Roly J.</creatorcontrib><creatorcontrib>Twin, Heather C.</creatorcontrib><creatorcontrib>Donohoe, Timothy J.</creatorcontrib><collection>Index Chemicus</collection><collection>Current Chemical Reactions</collection><collection>Web of Science - Science Citation Index Expanded - 2020</collection><collection>Web of Science Core Collection</collection><collection>Science Citation Index Expanded</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>Chamberlain, Anna E. R.</au><au>Paterson, Kieran J.</au><au>Armstrong, Roly J.</au><au>Twin, Heather C.</au><au>Donohoe, Timothy J.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A hydrogen borrowing annulation strategy for the stereocontrolled synthesis of saturated aza-heterocycles</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><stitle>CHEM COMMUN</stitle><addtitle>Chem Commun (Camb)</addtitle><date>2020-03-25</date><risdate>2020</risdate><volume>56</volume><issue>24</issue><spage>3563</spage><epage>3566</epage><pages>3563-3566</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>An iridium catalyzed method for the synthesis of saturated aza-heterocycles from amines and diols is reported. A wide range of substituted heterocycles can be obtained using this approach including products bearing substituents at the C2, C3 and C4 positions. Employing water as the solvent, enantiopure diols could undergo annulation with minimal racemization, enabling the synthesis of valuable enantioenriched C3 and C4-substituted saturated aza-heterocycles.</abstract><cop>CAMBRIDGE</cop><pub>Royal Soc Chemistry</pub><pmid>32104845</pmid><doi>10.1039/d0cc00903b</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0001-7088-6626</orcidid><orcidid>https://orcid.org/0000-0002-3759-061X</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1359-7345 |
| ispartof | Chemical communications (Cambridge, England), 2020-03, Vol.56 (24), p.3563-3566 |
| issn | 1359-7345 1364-548X |
| language | eng |
| recordid | cdi_proquest_miscellaneous_2366636505 |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Amines Chemical reactions Chemical synthesis Chemistry Chemistry, Multidisciplinary Diols Iridium Organic chemistry Physical Sciences Racemization Science & Technology Substitutes |
| title | A hydrogen borrowing annulation strategy for the stereocontrolled synthesis of saturated aza-heterocycles |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-15T22%3A18%3A25IST&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=A%20hydrogen%20borrowing%20annulation%20strategy%20for%20the%20stereocontrolled%20synthesis%20of%20saturated%20aza-heterocycles&rft.jtitle=Chemical%20communications%20(Cambridge,%20England)&rft.au=Chamberlain,%20Anna%20E.%20R.&rft.date=2020-03-25&rft.volume=56&rft.issue=24&rft.spage=3563&rft.epage=3566&rft.pages=3563-3566&rft.issn=1359-7345&rft.eissn=1364-548X&rft_id=info:doi/10.1039/d0cc00903b&rft_dat=%3Cproquest_cross%3E2382049767%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=2382049767&rft_id=info:pmid/32104845&rfr_iscdi=true |