Desymmetrization of meso-Cyclic Imides via Enantioselective Monohydrogenation
meso-Cyclic imides are monohydrogenated to form the corresponding hydroxy lactams in 88−97% ee using trans-[Ru((R)-BINAP)(H)2((R,R)-dpen)] and related compounds as catalysts with base in THF. The hydrogenation proceeds with high enantiogroup- and chemoselectivity, and it is a desymmetrization reacti...
Gespeichert in:
| Veröffentlicht in: | Journal of the American Chemical Society 2010-09, Vol.132 (37), p.12832-12834 |
|---|---|
| Hauptverfasser: | , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 12834 |
|---|---|
| container_issue | 37 |
| container_start_page | 12832 |
| container_title | Journal of the American Chemical Society |
| container_volume | 132 |
| creator | Takebayashi, Satoshi John, Jeremy M Bergens, Steven H |
| description | meso-Cyclic imides are monohydrogenated to form the corresponding hydroxy lactams in 88−97% ee using trans-[Ru((R)-BINAP)(H)2((R,R)-dpen)] and related compounds as catalysts with base in THF. The hydrogenation proceeds with high enantiogroup- and chemoselectivity, and it is a desymmetrization reaction, forming up to five stereogenic centers in one reaction. Conversion of a hydroxy lactam into the corresponding iminium ion followed by addition of indene extended the number of stereogenic centers from 5 to 7. |
| doi_str_mv | 10.1021/ja105783u |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_755160430</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>755160430</sourcerecordid><originalsourceid>FETCH-LOGICAL-a314t-f9071985853678e3d9aef76d7b5f5595a6cf20eeccd0b4f61db096291948cf003</originalsourceid><addsrcrecordid>eNpt0D1PwzAQBmALgWgpDPwBlAUhhoA_YjseUSlQqRULzJHjnMFVEpc4qRR-PSktnZhOJz33SvcidEnwHcGU3K80wVymrDtCY8Ipjjmh4hiNMcY0lqlgI3QWwmpYE5qSUzSiWLJEKTpGy0cIfVVB27hv3TpfR95GFQQfT3tTOhPNK1dAiDZOR7Na1wMJUIJp3Qaipa_9Z180_gPq3-NzdGJ1GeBiPyfo_Wn2Nn2JF6_P8-nDItaMJG1sFZZEpTzlTMgUWKE0WCkKmXPLueJaGEsxgDEFzhMrSJFjJagiKkmNxZhN0M0ud934rw5Cm1UuGChLXYPvQiY5JwInbCtvd9I0PoQGbLZuXKWbPiM425aXHcob7NU-tcsrKA7yr60BXO-ANiFb-a6phyf_CfoBkeJ2aw</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>755160430</pqid></control><display><type>article</type><title>Desymmetrization of meso-Cyclic Imides via Enantioselective Monohydrogenation</title><source>MEDLINE</source><source>American Chemical Society Journals</source><creator>Takebayashi, Satoshi ; John, Jeremy M ; Bergens, Steven H</creator><creatorcontrib>Takebayashi, Satoshi ; John, Jeremy M ; Bergens, Steven H</creatorcontrib><description>meso-Cyclic imides are monohydrogenated to form the corresponding hydroxy lactams in 88−97% ee using trans-[Ru((R)-BINAP)(H)2((R,R)-dpen)] and related compounds as catalysts with base in THF. The hydrogenation proceeds with high enantiogroup- and chemoselectivity, and it is a desymmetrization reaction, forming up to five stereogenic centers in one reaction. Conversion of a hydroxy lactam into the corresponding iminium ion followed by addition of indene extended the number of stereogenic centers from 5 to 7.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/ja105783u</identifier><identifier>PMID: 20734992</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Catalysis ; Hydrogenation ; Imides - chemistry ; Stereoisomerism ; Substrate Specificity</subject><ispartof>Journal of the American Chemical Society, 2010-09, Vol.132 (37), p.12832-12834</ispartof><rights>Copyright © 2010 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a314t-f9071985853678e3d9aef76d7b5f5595a6cf20eeccd0b4f61db096291948cf003</citedby><cites>FETCH-LOGICAL-a314t-f9071985853678e3d9aef76d7b5f5595a6cf20eeccd0b4f61db096291948cf003</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/ja105783u$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ja105783u$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20734992$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Takebayashi, Satoshi</creatorcontrib><creatorcontrib>John, Jeremy M</creatorcontrib><creatorcontrib>Bergens, Steven H</creatorcontrib><title>Desymmetrization of meso-Cyclic Imides via Enantioselective Monohydrogenation</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>meso-Cyclic imides are monohydrogenated to form the corresponding hydroxy lactams in 88−97% ee using trans-[Ru((R)-BINAP)(H)2((R,R)-dpen)] and related compounds as catalysts with base in THF. The hydrogenation proceeds with high enantiogroup- and chemoselectivity, and it is a desymmetrization reaction, forming up to five stereogenic centers in one reaction. Conversion of a hydroxy lactam into the corresponding iminium ion followed by addition of indene extended the number of stereogenic centers from 5 to 7.</description><subject>Catalysis</subject><subject>Hydrogenation</subject><subject>Imides - chemistry</subject><subject>Stereoisomerism</subject><subject>Substrate Specificity</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0D1PwzAQBmALgWgpDPwBlAUhhoA_YjseUSlQqRULzJHjnMFVEpc4qRR-PSktnZhOJz33SvcidEnwHcGU3K80wVymrDtCY8Ipjjmh4hiNMcY0lqlgI3QWwmpYE5qSUzSiWLJEKTpGy0cIfVVB27hv3TpfR95GFQQfT3tTOhPNK1dAiDZOR7Na1wMJUIJp3Qaipa_9Z180_gPq3-NzdGJ1GeBiPyfo_Wn2Nn2JF6_P8-nDItaMJG1sFZZEpTzlTMgUWKE0WCkKmXPLueJaGEsxgDEFzhMrSJFjJagiKkmNxZhN0M0ud934rw5Cm1UuGChLXYPvQiY5JwInbCtvd9I0PoQGbLZuXKWbPiM425aXHcob7NU-tcsrKA7yr60BXO-ANiFb-a6phyf_CfoBkeJ2aw</recordid><startdate>20100922</startdate><enddate>20100922</enddate><creator>Takebayashi, Satoshi</creator><creator>John, Jeremy M</creator><creator>Bergens, Steven 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></search><sort><creationdate>20100922</creationdate><title>Desymmetrization of meso-Cyclic Imides via Enantioselective Monohydrogenation</title><author>Takebayashi, Satoshi ; John, Jeremy M ; Bergens, Steven H</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a314t-f9071985853678e3d9aef76d7b5f5595a6cf20eeccd0b4f61db096291948cf003</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>Catalysis</topic><topic>Hydrogenation</topic><topic>Imides - chemistry</topic><topic>Stereoisomerism</topic><topic>Substrate Specificity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Takebayashi, Satoshi</creatorcontrib><creatorcontrib>John, Jeremy M</creatorcontrib><creatorcontrib>Bergens, Steven 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><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Takebayashi, Satoshi</au><au>John, Jeremy M</au><au>Bergens, Steven H</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Desymmetrization of meso-Cyclic Imides via Enantioselective Monohydrogenation</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2010-09-22</date><risdate>2010</risdate><volume>132</volume><issue>37</issue><spage>12832</spage><epage>12834</epage><pages>12832-12834</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><abstract>meso-Cyclic imides are monohydrogenated to form the corresponding hydroxy lactams in 88−97% ee using trans-[Ru((R)-BINAP)(H)2((R,R)-dpen)] and related compounds as catalysts with base in THF. The hydrogenation proceeds with high enantiogroup- and chemoselectivity, and it is a desymmetrization reaction, forming up to five stereogenic centers in one reaction. Conversion of a hydroxy lactam into the corresponding iminium ion followed by addition of indene extended the number of stereogenic centers from 5 to 7.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>20734992</pmid><doi>10.1021/ja105783u</doi><tpages>3</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0002-7863 |
| ispartof | Journal of the American Chemical Society, 2010-09, Vol.132 (37), p.12832-12834 |
| issn | 0002-7863 1520-5126 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_755160430 |
| source | MEDLINE; American Chemical Society Journals |
| subjects | Catalysis Hydrogenation Imides - chemistry Stereoisomerism Substrate Specificity |
| title | Desymmetrization of meso-Cyclic Imides via Enantioselective Monohydrogenation |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-03T15%3A24%3A12IST&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=Desymmetrization%20of%20meso-Cyclic%20Imides%20via%20Enantioselective%20Monohydrogenation&rft.jtitle=Journal%20of%20the%20American%20Chemical%20Society&rft.au=Takebayashi,%20Satoshi&rft.date=2010-09-22&rft.volume=132&rft.issue=37&rft.spage=12832&rft.epage=12834&rft.pages=12832-12834&rft.issn=0002-7863&rft.eissn=1520-5126&rft_id=info:doi/10.1021/ja105783u&rft_dat=%3Cproquest_cross%3E755160430%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=755160430&rft_id=info:pmid/20734992&rfr_iscdi=true |