Synthesis and Optical Resolution of Aminophosphines with Axially Chiral C(aryl)−N(amine) Bonds for Use as Ligands in Asymmetric Catalysis
N-Aryl indoline-type aminophosphines 1a−c were obtained in good yields by a nucleophilic aromatic substitution (SNAr) reaction followed by silane reduction. Aminophosphine 1d was also prepared from 2,3-difluorobenzaldehyde (4) via dimethylhydrazone. Optical resolution of C(aryl)−N(amine) bond atropi...
Gespeichert in:
| Veröffentlicht in: | Journal of organic chemistry 2006-09, Vol.71 (19), p.7346-7353 |
|---|---|
| Hauptverfasser: | , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 7353 |
|---|---|
| container_issue | 19 |
| container_start_page | 7346 |
| container_title | Journal of organic chemistry |
| container_volume | 71 |
| creator | Mino, Takashi Tanaka, Youichi Hattori, Youtaro Yabusaki, Toshihiro Saotome, Hiroaki Sakamoto, Masami Fujita, Tsutomu |
| description | N-Aryl indoline-type aminophosphines 1a−c were obtained in good yields by a nucleophilic aromatic substitution (SNAr) reaction followed by silane reduction. Aminophosphine 1d was also prepared from 2,3-difluorobenzaldehyde (4) via dimethylhydrazone. Optical resolution of C(aryl)−N(amine) bond atropisomers was achieved using (S)-(+)-di-μ-chlorobis[2-[(dimethylamino)ethyl]phenyl-C 2,N]dipalladium(II) ((S)-10). The determination of absolute configuration and the investigation of the rotation barrier for C(aryl)−N(amine) bond axial stability of an aminophosphine 1 are described. Finally, the ability of the chiral phosphine ligand 1 is demonstrated in a catalytic asymmetric reaction, such as a palladium-catalyzed asymmetric allylic alkylation of 1,3-diphenyl-2-propenyl acetate with dimethyl malonate (up to 95% ee). |
| doi_str_mv | 10.1021/jo061261f |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_68839300</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>68839300</sourcerecordid><originalsourceid>FETCH-LOGICAL-a381t-58d2d6c9dac45e23c23f3cb1afcd3bf50656c7a8f11e23ed7438ba4e4961918b3</originalsourceid><addsrcrecordid>eNptkc1u1DAURiMEokNhwQsgb0CdRcA_sZMshwgYpBGt6HRtOY5DXBI7-CaieQMkdjwiT4KrGXU2eGPJ9_jT5-MkeUnwW4IpeXfrsSBUkPZRsiKc4lSUOHucrDCmNGVUsLPkGcAtjotz_jQ5I6LkBaflKvl9vbipM2ABKdegy3GyWvXoqwHfz5P1DvkWbQbr_Nh5GDvrDKCfdurQ5s6qvl9Q1dkQb1QXKiz9-u-vP18uVOTNGr33rgHU-oBuwCAFaGe_qfsj69AGlmEwU7AaVWpS_RIbPE-etKoH8-K4nyc3Hz_sq226u_z0udrsUsUKMqW8aGgjdNkonXFDmaasZbomqtUNq1uOBRc6V0VLSJyaJs9YUavMZKUgJSlqdp68OeSOwf-YDUxysKBN3ytn_AxSFAUrGcYRXB9AHTxAMK0cgx3iOyXB8t68fDAf2VfH0LkeTHMij6oj8PoIKIiK26CctnDiClyW8cMilx44C5O5e5ir8F2KnOVc7q-u5XbP-H6Xb-XVKVdpiH3m4KK7_xT8B8mOqLs</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>68839300</pqid></control><display><type>article</type><title>Synthesis and Optical Resolution of Aminophosphines with Axially Chiral C(aryl)−N(amine) Bonds for Use as Ligands in Asymmetric Catalysis</title><source>American Chemical Society Journals</source><creator>Mino, Takashi ; Tanaka, Youichi ; Hattori, Youtaro ; Yabusaki, Toshihiro ; Saotome, Hiroaki ; Sakamoto, Masami ; Fujita, Tsutomu</creator><creatorcontrib>Mino, Takashi ; Tanaka, Youichi ; Hattori, Youtaro ; Yabusaki, Toshihiro ; Saotome, Hiroaki ; Sakamoto, Masami ; Fujita, Tsutomu</creatorcontrib><description>N-Aryl indoline-type aminophosphines 1a−c were obtained in good yields by a nucleophilic aromatic substitution (SNAr) reaction followed by silane reduction. Aminophosphine 1d was also prepared from 2,3-difluorobenzaldehyde (4) via dimethylhydrazone. Optical resolution of C(aryl)−N(amine) bond atropisomers was achieved using (S)-(+)-di-μ-chlorobis[2-[(dimethylamino)ethyl]phenyl-C 2,N]dipalladium(II) ((S)-10). The determination of absolute configuration and the investigation of the rotation barrier for C(aryl)−N(amine) bond axial stability of an aminophosphine 1 are described. Finally, the ability of the chiral phosphine ligand 1 is demonstrated in a catalytic asymmetric reaction, such as a palladium-catalyzed asymmetric allylic alkylation of 1,3-diphenyl-2-propenyl acetate with dimethyl malonate (up to 95% ee).</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo061261f</identifier><identifier>PMID: 16958529</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Chemistry ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with only one n hetero atom and condensed derivatives ; Organic chemistry ; Preparations and properties</subject><ispartof>Journal of organic chemistry, 2006-09, Vol.71 (19), p.7346-7353</ispartof><rights>Copyright © 2006 American Chemical Society</rights><rights>2007 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a381t-58d2d6c9dac45e23c23f3cb1afcd3bf50656c7a8f11e23ed7438ba4e4961918b3</citedby><cites>FETCH-LOGICAL-a381t-58d2d6c9dac45e23c23f3cb1afcd3bf50656c7a8f11e23ed7438ba4e4961918b3</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/jo061261f$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo061261f$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=18099002$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16958529$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Mino, Takashi</creatorcontrib><creatorcontrib>Tanaka, Youichi</creatorcontrib><creatorcontrib>Hattori, Youtaro</creatorcontrib><creatorcontrib>Yabusaki, Toshihiro</creatorcontrib><creatorcontrib>Saotome, Hiroaki</creatorcontrib><creatorcontrib>Sakamoto, Masami</creatorcontrib><creatorcontrib>Fujita, Tsutomu</creatorcontrib><title>Synthesis and Optical Resolution of Aminophosphines with Axially Chiral C(aryl)−N(amine) Bonds for Use as Ligands in Asymmetric Catalysis</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>N-Aryl indoline-type aminophosphines 1a−c were obtained in good yields by a nucleophilic aromatic substitution (SNAr) reaction followed by silane reduction. Aminophosphine 1d was also prepared from 2,3-difluorobenzaldehyde (4) via dimethylhydrazone. Optical resolution of C(aryl)−N(amine) bond atropisomers was achieved using (S)-(+)-di-μ-chlorobis[2-[(dimethylamino)ethyl]phenyl-C 2,N]dipalladium(II) ((S)-10). The determination of absolute configuration and the investigation of the rotation barrier for C(aryl)−N(amine) bond axial stability of an aminophosphine 1 are described. Finally, the ability of the chiral phosphine ligand 1 is demonstrated in a catalytic asymmetric reaction, such as a palladium-catalyzed asymmetric allylic alkylation of 1,3-diphenyl-2-propenyl acetate with dimethyl malonate (up to 95% ee).</description><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with only one n hetero atom and condensed derivatives</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><recordid>eNptkc1u1DAURiMEokNhwQsgb0CdRcA_sZMshwgYpBGt6HRtOY5DXBI7-CaieQMkdjwiT4KrGXU2eGPJ9_jT5-MkeUnwW4IpeXfrsSBUkPZRsiKc4lSUOHucrDCmNGVUsLPkGcAtjotz_jQ5I6LkBaflKvl9vbipM2ABKdegy3GyWvXoqwHfz5P1DvkWbQbr_Nh5GDvrDKCfdurQ5s6qvl9Q1dkQb1QXKiz9-u-vP18uVOTNGr33rgHU-oBuwCAFaGe_qfsj69AGlmEwU7AaVWpS_RIbPE-etKoH8-K4nyc3Hz_sq226u_z0udrsUsUKMqW8aGgjdNkonXFDmaasZbomqtUNq1uOBRc6V0VLSJyaJs9YUavMZKUgJSlqdp68OeSOwf-YDUxysKBN3ytn_AxSFAUrGcYRXB9AHTxAMK0cgx3iOyXB8t68fDAf2VfH0LkeTHMij6oj8PoIKIiK26CctnDiClyW8cMilx44C5O5e5ir8F2KnOVc7q-u5XbP-H6Xb-XVKVdpiH3m4KK7_xT8B8mOqLs</recordid><startdate>20060915</startdate><enddate>20060915</enddate><creator>Mino, Takashi</creator><creator>Tanaka, Youichi</creator><creator>Hattori, Youtaro</creator><creator>Yabusaki, Toshihiro</creator><creator>Saotome, Hiroaki</creator><creator>Sakamoto, Masami</creator><creator>Fujita, Tsutomu</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20060915</creationdate><title>Synthesis and Optical Resolution of Aminophosphines with Axially Chiral C(aryl)−N(amine) Bonds for Use as Ligands in Asymmetric Catalysis</title><author>Mino, Takashi ; Tanaka, Youichi ; Hattori, Youtaro ; Yabusaki, Toshihiro ; Saotome, Hiroaki ; Sakamoto, Masami ; Fujita, Tsutomu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a381t-58d2d6c9dac45e23c23f3cb1afcd3bf50656c7a8f11e23ed7438ba4e4961918b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with only one n hetero atom and condensed derivatives</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mino, Takashi</creatorcontrib><creatorcontrib>Tanaka, Youichi</creatorcontrib><creatorcontrib>Hattori, Youtaro</creatorcontrib><creatorcontrib>Yabusaki, Toshihiro</creatorcontrib><creatorcontrib>Saotome, Hiroaki</creatorcontrib><creatorcontrib>Sakamoto, Masami</creatorcontrib><creatorcontrib>Fujita, Tsutomu</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Mino, Takashi</au><au>Tanaka, Youichi</au><au>Hattori, Youtaro</au><au>Yabusaki, Toshihiro</au><au>Saotome, Hiroaki</au><au>Sakamoto, Masami</au><au>Fujita, Tsutomu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Optical Resolution of Aminophosphines with Axially Chiral C(aryl)−N(amine) Bonds for Use as Ligands in Asymmetric Catalysis</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2006-09-15</date><risdate>2006</risdate><volume>71</volume><issue>19</issue><spage>7346</spage><epage>7353</epage><pages>7346-7353</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>N-Aryl indoline-type aminophosphines 1a−c were obtained in good yields by a nucleophilic aromatic substitution (SNAr) reaction followed by silane reduction. Aminophosphine 1d was also prepared from 2,3-difluorobenzaldehyde (4) via dimethylhydrazone. Optical resolution of C(aryl)−N(amine) bond atropisomers was achieved using (S)-(+)-di-μ-chlorobis[2-[(dimethylamino)ethyl]phenyl-C 2,N]dipalladium(II) ((S)-10). The determination of absolute configuration and the investigation of the rotation barrier for C(aryl)−N(amine) bond axial stability of an aminophosphine 1 are described. Finally, the ability of the chiral phosphine ligand 1 is demonstrated in a catalytic asymmetric reaction, such as a palladium-catalyzed asymmetric allylic alkylation of 1,3-diphenyl-2-propenyl acetate with dimethyl malonate (up to 95% ee).</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>16958529</pmid><doi>10.1021/jo061261f</doi><tpages>8</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0022-3263 |
| ispartof | Journal of organic chemistry, 2006-09, Vol.71 (19), p.7346-7353 |
| issn | 0022-3263 1520-6904 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_68839300 |
| source | American Chemical Society Journals |
| subjects | Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Organic chemistry Preparations and properties |
| title | Synthesis and Optical Resolution of Aminophosphines with Axially Chiral C(aryl)−N(amine) Bonds for Use as Ligands in Asymmetric Catalysis |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-27T11%3A48%3A33IST&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=Synthesis%20and%20Optical%20Resolution%20of%20Aminophosphines%20with%20Axially%20Chiral%20C(aryl)%E2%88%92N(amine)%20Bonds%20for%20Use%20as%20Ligands%20in%20Asymmetric%20Catalysis&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Mino,%20Takashi&rft.date=2006-09-15&rft.volume=71&rft.issue=19&rft.spage=7346&rft.epage=7353&rft.pages=7346-7353&rft.issn=0022-3263&rft.eissn=1520-6904&rft.coden=JOCEAH&rft_id=info:doi/10.1021/jo061261f&rft_dat=%3Cproquest_cross%3E68839300%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=68839300&rft_id=info:pmid/16958529&rfr_iscdi=true |