H₈-BINOL chiral imidodiphosphoric acid catalyzed highly enantioselective aza-Friedel-Crafts reactions of pyrroles and enamides/imines
The first enantioselective aza-Friedel-Crafts reaction between pyrroles and enamides has been achieved by using a novel H8-BINOL-type imidodiphosphoric acid catalyst. This methodology was also applied to the highly enantioselective aza-Friedel-Crafts reaction between pyrroles and imines. The catalys...
Gespeichert in:
Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2015-05, Vol.51 (38), p.8054-8057 |
---|---|
Hauptverfasser: | , , , , , , |
Format: | Artikel |
Sprache: | eng |
Schlagworte: | |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
container_end_page | 8057 |
---|---|
container_issue | 38 |
container_start_page | 8054 |
container_title | Chemical communications (Cambridge, England) |
container_volume | 51 |
creator | Wu, Kun Zhuo, Ming-Hua Sha, Di Fan, Yan-Sen An, Dong Jiang, Yi-Jun Zhang, Suoqin |
description | The first enantioselective aza-Friedel-Crafts reaction between pyrroles and enamides has been achieved by using a novel H8-BINOL-type imidodiphosphoric acid catalyst. This methodology was also applied to the highly enantioselective aza-Friedel-Crafts reaction between pyrroles and imines. The catalyst loadings in these two reactions are low (0.3-2 mol%). Both processes are amenable to gram scales. |
doi_str_mv | 10.1039/c5cc00685f |
format | Article |
fullrecord | <record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_proquest_miscellaneous_1676607061</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1676607061</sourcerecordid><originalsourceid>FETCH-LOGICAL-j192t-e991ad8adf2776941f8d415e85558252f3cc2ee7f02a7951475b68e576b8ab4c3</originalsourceid><addsrcrecordid>eNo1kM1OwzAQhC0kREvhwgMgH7mExknsOEeoKK1U0QtI3KKNvSGunB_sFCk9coHn5EkIAlZazWG-nZGWkAsWXrMwzuaKKxWGQvLyiExZLJKAJ_J5Qk6934XjMC5PyCTiUiRJLKbkY_X1_hncrh-2G6oq48BSUxvdatNVrR_XGUVBGU0V9GCHA2pamZfKDhQbaHrTerSoevOGFA4QLJ1BjTZYOCh7Tx3C6LWNp21Ju8G51qKn0Oif67EH_Xysa9CfkeMSrMfzP52Rp-Xd42IVbLb368XNJtixLOoDzDIGWoIuozQVWcJKqRPGUXLOZcSjMlYqQkzLMII04yxJeSEk8lQUEopExTNy9ZvbufZ1j77Pa-MVWgsNtnufM5EKEaahYCN6-Yfuixp13jlTgxvy_-fF3466ceM</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1676607061</pqid></control><display><type>article</type><title>H₈-BINOL chiral imidodiphosphoric acid catalyzed highly enantioselective aza-Friedel-Crafts reactions of pyrroles and enamides/imines</title><source>MEDLINE</source><source>Royal Society Of Chemistry Journals</source><source>Alma/SFX Local Collection</source><creator>Wu, Kun ; Zhuo, Ming-Hua ; Sha, Di ; Fan, Yan-Sen ; An, Dong ; Jiang, Yi-Jun ; Zhang, Suoqin</creator><creatorcontrib>Wu, Kun ; Zhuo, Ming-Hua ; Sha, Di ; Fan, Yan-Sen ; An, Dong ; Jiang, Yi-Jun ; Zhang, Suoqin</creatorcontrib><description>The first enantioselective aza-Friedel-Crafts reaction between pyrroles and enamides has been achieved by using a novel H8-BINOL-type imidodiphosphoric acid catalyst. This methodology was also applied to the highly enantioselective aza-Friedel-Crafts reaction between pyrroles and imines. The catalyst loadings in these two reactions are low (0.3-2 mol%). Both processes are amenable to gram scales.</description><identifier>EISSN: 1364-548X</identifier><identifier>DOI: 10.1039/c5cc00685f</identifier><identifier>PMID: 25864436</identifier><language>eng</language><publisher>England</publisher><subject>Amides - chemistry ; Amines - chemical synthesis ; Amines - chemistry ; Catalysis ; Diphosphonates - chemistry ; Imines - chemistry ; Molecular Structure ; Naphthols - chemistry ; Pyrroles - chemistry ; Stereoisomerism</subject><ispartof>Chemical communications (Cambridge, England), 2015-05, Vol.51 (38), p.8054-8057</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>315,781,785,27929,27930</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25864436$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wu, Kun</creatorcontrib><creatorcontrib>Zhuo, Ming-Hua</creatorcontrib><creatorcontrib>Sha, Di</creatorcontrib><creatorcontrib>Fan, Yan-Sen</creatorcontrib><creatorcontrib>An, Dong</creatorcontrib><creatorcontrib>Jiang, Yi-Jun</creatorcontrib><creatorcontrib>Zhang, Suoqin</creatorcontrib><title>H₈-BINOL chiral imidodiphosphoric acid catalyzed highly enantioselective aza-Friedel-Crafts reactions of pyrroles and enamides/imines</title><title>Chemical communications (Cambridge, England)</title><addtitle>Chem Commun (Camb)</addtitle><description>The first enantioselective aza-Friedel-Crafts reaction between pyrroles and enamides has been achieved by using a novel H8-BINOL-type imidodiphosphoric acid catalyst. This methodology was also applied to the highly enantioselective aza-Friedel-Crafts reaction between pyrroles and imines. The catalyst loadings in these two reactions are low (0.3-2 mol%). Both processes are amenable to gram scales.</description><subject>Amides - chemistry</subject><subject>Amines - chemical synthesis</subject><subject>Amines - chemistry</subject><subject>Catalysis</subject><subject>Diphosphonates - chemistry</subject><subject>Imines - chemistry</subject><subject>Molecular Structure</subject><subject>Naphthols - chemistry</subject><subject>Pyrroles - chemistry</subject><subject>Stereoisomerism</subject><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNo1kM1OwzAQhC0kREvhwgMgH7mExknsOEeoKK1U0QtI3KKNvSGunB_sFCk9coHn5EkIAlZazWG-nZGWkAsWXrMwzuaKKxWGQvLyiExZLJKAJ_J5Qk6934XjMC5PyCTiUiRJLKbkY_X1_hncrh-2G6oq48BSUxvdatNVrR_XGUVBGU0V9GCHA2pamZfKDhQbaHrTerSoevOGFA4QLJ1BjTZYOCh7Tx3C6LWNp21Ju8G51qKn0Oif67EH_Xysa9CfkeMSrMfzP52Rp-Xd42IVbLb368XNJtixLOoDzDIGWoIuozQVWcJKqRPGUXLOZcSjMlYqQkzLMII04yxJeSEk8lQUEopExTNy9ZvbufZ1j77Pa-MVWgsNtnufM5EKEaahYCN6-Yfuixp13jlTgxvy_-fF3466ceM</recordid><startdate>20150511</startdate><enddate>20150511</enddate><creator>Wu, Kun</creator><creator>Zhuo, Ming-Hua</creator><creator>Sha, Di</creator><creator>Fan, Yan-Sen</creator><creator>An, Dong</creator><creator>Jiang, Yi-Jun</creator><creator>Zhang, Suoqin</creator><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>20150511</creationdate><title>H₈-BINOL chiral imidodiphosphoric acid catalyzed highly enantioselective aza-Friedel-Crafts reactions of pyrroles and enamides/imines</title><author>Wu, Kun ; Zhuo, Ming-Hua ; Sha, Di ; Fan, Yan-Sen ; An, Dong ; Jiang, Yi-Jun ; Zhang, Suoqin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-j192t-e991ad8adf2776941f8d415e85558252f3cc2ee7f02a7951475b68e576b8ab4c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Amides - chemistry</topic><topic>Amines - chemical synthesis</topic><topic>Amines - chemistry</topic><topic>Catalysis</topic><topic>Diphosphonates - chemistry</topic><topic>Imines - chemistry</topic><topic>Molecular Structure</topic><topic>Naphthols - chemistry</topic><topic>Pyrroles - chemistry</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wu, Kun</creatorcontrib><creatorcontrib>Zhuo, Ming-Hua</creatorcontrib><creatorcontrib>Sha, Di</creatorcontrib><creatorcontrib>Fan, Yan-Sen</creatorcontrib><creatorcontrib>An, Dong</creatorcontrib><creatorcontrib>Jiang, Yi-Jun</creatorcontrib><creatorcontrib>Zhang, Suoqin</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical communications (Cambridge, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wu, Kun</au><au>Zhuo, Ming-Hua</au><au>Sha, Di</au><au>Fan, Yan-Sen</au><au>An, Dong</au><au>Jiang, Yi-Jun</au><au>Zhang, Suoqin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>H₈-BINOL chiral imidodiphosphoric acid catalyzed highly enantioselective aza-Friedel-Crafts reactions of pyrroles and enamides/imines</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><addtitle>Chem Commun (Camb)</addtitle><date>2015-05-11</date><risdate>2015</risdate><volume>51</volume><issue>38</issue><spage>8054</spage><epage>8057</epage><pages>8054-8057</pages><eissn>1364-548X</eissn><abstract>The first enantioselective aza-Friedel-Crafts reaction between pyrroles and enamides has been achieved by using a novel H8-BINOL-type imidodiphosphoric acid catalyst. This methodology was also applied to the highly enantioselective aza-Friedel-Crafts reaction between pyrroles and imines. The catalyst loadings in these two reactions are low (0.3-2 mol%). Both processes are amenable to gram scales.</abstract><cop>England</cop><pmid>25864436</pmid><doi>10.1039/c5cc00685f</doi><tpages>4</tpages></addata></record> |
fulltext | fulltext |
identifier | EISSN: 1364-548X |
ispartof | Chemical communications (Cambridge, England), 2015-05, Vol.51 (38), p.8054-8057 |
issn | 1364-548X |
language | eng |
recordid | cdi_proquest_miscellaneous_1676607061 |
source | MEDLINE; Royal Society Of Chemistry Journals; Alma/SFX Local Collection |
subjects | Amides - chemistry Amines - chemical synthesis Amines - chemistry Catalysis Diphosphonates - chemistry Imines - chemistry Molecular Structure Naphthols - chemistry Pyrroles - chemistry Stereoisomerism |
title | H₈-BINOL chiral imidodiphosphoric acid catalyzed highly enantioselective aza-Friedel-Crafts reactions of pyrroles and enamides/imines |
url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-12T13%3A57%3A14IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_pubme&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=H%E2%82%88-BINOL%20chiral%20imidodiphosphoric%20acid%20catalyzed%20highly%20enantioselective%20aza-Friedel-Crafts%20reactions%20of%20pyrroles%20and%20enamides/imines&rft.jtitle=Chemical%20communications%20(Cambridge,%20England)&rft.au=Wu,%20Kun&rft.date=2015-05-11&rft.volume=51&rft.issue=38&rft.spage=8054&rft.epage=8057&rft.pages=8054-8057&rft.eissn=1364-548X&rft_id=info:doi/10.1039/c5cc00685f&rft_dat=%3Cproquest_pubme%3E1676607061%3C/proquest_pubme%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1676607061&rft_id=info:pmid/25864436&rfr_iscdi=true |