Enantioselective [4 + 2] Cycloaddition of Cyclic N‑Sulfimines and Acyclic Enones or Ynones: A Concise Route to Sulfamidate-Fused 2,6-Disubstituted Piperidin-4-ones
A concise route to valuable sulfamate-fused 2,6-disubstituted piperidin-4-ones or 2,3-dihydropyridin-4(1H)-ones in good yield with high diastereo- and enantioselectivity is presented. The combination of chiral primary amine and o-fluorobenzoic acid efficiently promoted an asymmetric [4 + 2] cycloadd...
Gespeichert in:
| Veröffentlicht in: | Organic letters 2013-12, Vol.15 (23), p.6090-6093 |
|---|---|
| Hauptverfasser: | , , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 6093 |
|---|---|
| container_issue | 23 |
| container_start_page | 6090 |
| container_title | Organic letters |
| container_volume | 15 |
| creator | Liu, Yong Kang, Tai-Ran Liu, Quan-Zhong Chen, Lian-Mei Wang, Ya-Chuan Liu, Jie Xie, Yong-Mei Yang, Jin-Liang He, Long |
| description | A concise route to valuable sulfamate-fused 2,6-disubstituted piperidin-4-ones or 2,3-dihydropyridin-4(1H)-ones in good yield with high diastereo- and enantioselectivity is presented. The combination of chiral primary amine and o-fluorobenzoic acid efficiently promoted an asymmetric [4 + 2] cycloaddition reaction of N-sulfonylimines and enones or ynones. The cycloaddition reaction between cyclic N-sulfonylimines and ynones is first reported. |
| doi_str_mv | 10.1021/ol402977w |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1499131019</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1499131019</sourcerecordid><originalsourceid>FETCH-LOGICAL-a381t-f7d55bfa35d37f86bdbfc1c296429879d9f99ac60c91739151d31df731ecf3b63</originalsourceid><addsrcrecordid>eNptkctOGzEUhq0KVGjKghdA3iC1gik-9lzi7qKQtJWigrgsEEIjjy-S0Ywdxh6q7HiFPgQv1idhcmlWrM7R_3_nl45-hA6BfANC4czXKaG8KP58QPuQUZYUJKM72z0ne-hTCI-EQK_wj2iPphQyRvN99DpxwkXrg661jPZZ4_sUn2D6gMcLWXuhlO1dh71ZCVbi3_9e_l53tbGNdTpg4RQeybU1cX4p-RbfrbbveITH3kkbNL7yXdQ4ery8FY1VIupk2gWtMD3Nk3MbuipEG3tK4Us7161V1iVpsgz6jHaNqIM-2MwBup1ObsY_k9nFj1_j0SwRbAgxMYXKssoIlilWmGFeqcpIkJTnKeXDgituOBcyJ5JDwThkoBgoUzDQ0rAqZwP0ZZ07b_1Tp0MsGxukrmvhtO9CCSnnwIAA79Gva1S2PoRWm3Le2ka0ixJIuWyl3LbSs0eb2K5qtNqS_2vogeM1IGQoH33Xuv7Ld4LeAAJjlWE</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1499131019</pqid></control><display><type>article</type><title>Enantioselective [4 + 2] Cycloaddition of Cyclic N‑Sulfimines and Acyclic Enones or Ynones: A Concise Route to Sulfamidate-Fused 2,6-Disubstituted Piperidin-4-ones</title><source>MEDLINE</source><source>American Chemical Society Journals</source><creator>Liu, Yong ; Kang, Tai-Ran ; Liu, Quan-Zhong ; Chen, Lian-Mei ; Wang, Ya-Chuan ; Liu, Jie ; Xie, Yong-Mei ; Yang, Jin-Liang ; He, Long</creator><creatorcontrib>Liu, Yong ; Kang, Tai-Ran ; Liu, Quan-Zhong ; Chen, Lian-Mei ; Wang, Ya-Chuan ; Liu, Jie ; Xie, Yong-Mei ; Yang, Jin-Liang ; He, Long</creatorcontrib><description>A concise route to valuable sulfamate-fused 2,6-disubstituted piperidin-4-ones or 2,3-dihydropyridin-4(1H)-ones in good yield with high diastereo- and enantioselectivity is presented. The combination of chiral primary amine and o-fluorobenzoic acid efficiently promoted an asymmetric [4 + 2] cycloaddition reaction of N-sulfonylimines and enones or ynones. The cycloaddition reaction between cyclic N-sulfonylimines and ynones is first reported.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol402977w</identifier><identifier>PMID: 24215326</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Amines - chemistry ; Catalysis ; Cyclization ; Cycloaddition Reaction ; Imines - chemistry ; Ketones - chemistry ; Molecular Structure ; Piperidones - chemical synthesis ; Piperidones - chemistry ; Stereoisomerism ; Sulfones - chemical synthesis ; Sulfones - chemistry</subject><ispartof>Organic letters, 2013-12, Vol.15 (23), p.6090-6093</ispartof><rights>Copyright © 2013 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a381t-f7d55bfa35d37f86bdbfc1c296429879d9f99ac60c91739151d31df731ecf3b63</citedby><cites>FETCH-LOGICAL-a381t-f7d55bfa35d37f86bdbfc1c296429879d9f99ac60c91739151d31df731ecf3b63</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/ol402977w$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol402977w$$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/24215326$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Liu, Yong</creatorcontrib><creatorcontrib>Kang, Tai-Ran</creatorcontrib><creatorcontrib>Liu, Quan-Zhong</creatorcontrib><creatorcontrib>Chen, Lian-Mei</creatorcontrib><creatorcontrib>Wang, Ya-Chuan</creatorcontrib><creatorcontrib>Liu, Jie</creatorcontrib><creatorcontrib>Xie, Yong-Mei</creatorcontrib><creatorcontrib>Yang, Jin-Liang</creatorcontrib><creatorcontrib>He, Long</creatorcontrib><title>Enantioselective [4 + 2] Cycloaddition of Cyclic N‑Sulfimines and Acyclic Enones or Ynones: A Concise Route to Sulfamidate-Fused 2,6-Disubstituted Piperidin-4-ones</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>A concise route to valuable sulfamate-fused 2,6-disubstituted piperidin-4-ones or 2,3-dihydropyridin-4(1H)-ones in good yield with high diastereo- and enantioselectivity is presented. The combination of chiral primary amine and o-fluorobenzoic acid efficiently promoted an asymmetric [4 + 2] cycloaddition reaction of N-sulfonylimines and enones or ynones. The cycloaddition reaction between cyclic N-sulfonylimines and ynones is first reported.</description><subject>Amines - chemistry</subject><subject>Catalysis</subject><subject>Cyclization</subject><subject>Cycloaddition Reaction</subject><subject>Imines - chemistry</subject><subject>Ketones - chemistry</subject><subject>Molecular Structure</subject><subject>Piperidones - chemical synthesis</subject><subject>Piperidones - chemistry</subject><subject>Stereoisomerism</subject><subject>Sulfones - chemical synthesis</subject><subject>Sulfones - chemistry</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkctOGzEUhq0KVGjKghdA3iC1gik-9lzi7qKQtJWigrgsEEIjjy-S0Ywdxh6q7HiFPgQv1idhcmlWrM7R_3_nl45-hA6BfANC4czXKaG8KP58QPuQUZYUJKM72z0ne-hTCI-EQK_wj2iPphQyRvN99DpxwkXrg661jPZZ4_sUn2D6gMcLWXuhlO1dh71ZCVbi3_9e_l53tbGNdTpg4RQeybU1cX4p-RbfrbbveITH3kkbNL7yXdQ4ery8FY1VIupk2gWtMD3Nk3MbuipEG3tK4Us7161V1iVpsgz6jHaNqIM-2MwBup1ObsY_k9nFj1_j0SwRbAgxMYXKssoIlilWmGFeqcpIkJTnKeXDgituOBcyJ5JDwThkoBgoUzDQ0rAqZwP0ZZ07b_1Tp0MsGxukrmvhtO9CCSnnwIAA79Gva1S2PoRWm3Le2ka0ixJIuWyl3LbSs0eb2K5qtNqS_2vogeM1IGQoH33Xuv7Ld4LeAAJjlWE</recordid><startdate>20131206</startdate><enddate>20131206</enddate><creator>Liu, Yong</creator><creator>Kang, Tai-Ran</creator><creator>Liu, Quan-Zhong</creator><creator>Chen, Lian-Mei</creator><creator>Wang, Ya-Chuan</creator><creator>Liu, Jie</creator><creator>Xie, Yong-Mei</creator><creator>Yang, Jin-Liang</creator><creator>He, Long</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>20131206</creationdate><title>Enantioselective [4 + 2] Cycloaddition of Cyclic N‑Sulfimines and Acyclic Enones or Ynones: A Concise Route to Sulfamidate-Fused 2,6-Disubstituted Piperidin-4-ones</title><author>Liu, Yong ; Kang, Tai-Ran ; Liu, Quan-Zhong ; Chen, Lian-Mei ; Wang, Ya-Chuan ; Liu, Jie ; Xie, Yong-Mei ; Yang, Jin-Liang ; He, Long</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a381t-f7d55bfa35d37f86bdbfc1c296429879d9f99ac60c91739151d31df731ecf3b63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Amines - chemistry</topic><topic>Catalysis</topic><topic>Cyclization</topic><topic>Cycloaddition Reaction</topic><topic>Imines - chemistry</topic><topic>Ketones - chemistry</topic><topic>Molecular Structure</topic><topic>Piperidones - chemical synthesis</topic><topic>Piperidones - chemistry</topic><topic>Stereoisomerism</topic><topic>Sulfones - chemical synthesis</topic><topic>Sulfones - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Liu, Yong</creatorcontrib><creatorcontrib>Kang, Tai-Ran</creatorcontrib><creatorcontrib>Liu, Quan-Zhong</creatorcontrib><creatorcontrib>Chen, Lian-Mei</creatorcontrib><creatorcontrib>Wang, Ya-Chuan</creatorcontrib><creatorcontrib>Liu, Jie</creatorcontrib><creatorcontrib>Xie, Yong-Mei</creatorcontrib><creatorcontrib>Yang, Jin-Liang</creatorcontrib><creatorcontrib>He, Long</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>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Liu, Yong</au><au>Kang, Tai-Ran</au><au>Liu, Quan-Zhong</au><au>Chen, Lian-Mei</au><au>Wang, Ya-Chuan</au><au>Liu, Jie</au><au>Xie, Yong-Mei</au><au>Yang, Jin-Liang</au><au>He, Long</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enantioselective [4 + 2] Cycloaddition of Cyclic N‑Sulfimines and Acyclic Enones or Ynones: A Concise Route to Sulfamidate-Fused 2,6-Disubstituted Piperidin-4-ones</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2013-12-06</date><risdate>2013</risdate><volume>15</volume><issue>23</issue><spage>6090</spage><epage>6093</epage><pages>6090-6093</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>A concise route to valuable sulfamate-fused 2,6-disubstituted piperidin-4-ones or 2,3-dihydropyridin-4(1H)-ones in good yield with high diastereo- and enantioselectivity is presented. The combination of chiral primary amine and o-fluorobenzoic acid efficiently promoted an asymmetric [4 + 2] cycloaddition reaction of N-sulfonylimines and enones or ynones. The cycloaddition reaction between cyclic N-sulfonylimines and ynones is first reported.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>24215326</pmid><doi>10.1021/ol402977w</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2013-12, Vol.15 (23), p.6090-6093 |
| issn | 1523-7060 1523-7052 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1499131019 |
| source | MEDLINE; American Chemical Society Journals |
| subjects | Amines - chemistry Catalysis Cyclization Cycloaddition Reaction Imines - chemistry Ketones - chemistry Molecular Structure Piperidones - chemical synthesis Piperidones - chemistry Stereoisomerism Sulfones - chemical synthesis Sulfones - chemistry |
| title | Enantioselective [4 + 2] Cycloaddition of Cyclic N‑Sulfimines and Acyclic Enones or Ynones: A Concise Route to Sulfamidate-Fused 2,6-Disubstituted Piperidin-4-ones |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-07T18%3A36%3A39IST&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=Enantioselective%20%5B4%20+%202%5D%20Cycloaddition%20of%20Cyclic%20N%E2%80%91Sulfimines%20and%20Acyclic%20Enones%20or%20Ynones:%20A%20Concise%20Route%20to%20Sulfamidate-Fused%202,6-Disubstituted%20Piperidin-4-ones&rft.jtitle=Organic%20letters&rft.au=Liu,%20Yong&rft.date=2013-12-06&rft.volume=15&rft.issue=23&rft.spage=6090&rft.epage=6093&rft.pages=6090-6093&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/ol402977w&rft_dat=%3Cproquest_cross%3E1499131019%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=1499131019&rft_id=info:pmid/24215326&rfr_iscdi=true |