Pd-Catalyzed Dearomative Asymmetric Allylic Alkylation of Naphthols with Alkoxyallenes

An Pd-catalyzed linear selective intermolecular asymmetric dearomative allylic alkylation reaction of naphthols with alkoxyallenes under mild reaction conditions is reported. The transformation is successfully promoted by Pd2(dba)3 and chiral Trost ligand, and provides a general atom-efficient proto...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of organic chemistry 2020-06, Vol.85 (12), p.7896-7904
Hauptverfasser: Hu, Jinjin, Pan, Shulei, Zhu, Shuai, Yu, Peiyuan, Xu, Ruigang, Zhong, Guofu, Zeng, Xiaofei
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 7904
container_issue 12
container_start_page 7896
container_title Journal of organic chemistry
container_volume 85
creator Hu, Jinjin
Pan, Shulei
Zhu, Shuai
Yu, Peiyuan
Xu, Ruigang
Zhong, Guofu
Zeng, Xiaofei
description An Pd-catalyzed linear selective intermolecular asymmetric dearomative allylic alkylation reaction of naphthols with alkoxyallenes under mild reaction conditions is reported. The transformation is successfully promoted by Pd2(dba)3 and chiral Trost ligand, and provides a general atom-efficient protocol to obtain various β-naphthalenones bearing an all carbon quaternary stereogenic center in good yields, chemo- and stereoselectivities.
doi_str_mv 10.1021/acs.joc.0c00582
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2408204344</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2408204344</sourcerecordid><originalsourceid>FETCH-LOGICAL-c297t-7d1b3413bd23948bb930c90828d977a530ab6df7885b8d6eabf93706c4536a553</originalsourceid><addsrcrecordid>eNo9kDtPwzAUhS0EoqUws6GMLGlv_IozVuUpVcAArJZfUVOcusQpEH49KS3c5Qznu2f4EDrPYJwBzibKxPEymDEYACbwARpmDEPKC6CHaAiAcUowJwN0EuMS-mOMHaMBwZRzTsUQvT7ZdKZa5btvZ5Mrp5pQq7b6cMk0dnXt2qYyydT7zv_mW-f7NqySUCYPar1oF8HH5LNqF9syfHXKe7dy8RQdlcpHd7bPEXq5uX6e3aXzx9v72XSeGlzkbZrbTBOaEW0xKajQuiBgChBY2CLPFSOgNLdlLgTTwnKndFmQHLihjHDFGBmhy93uugnvGxdbWVfROO_VyoVNlJj2Y0AJpT062aGmCTE2rpTrpqpV08kM5Fam7GXKXqbcy-w_LvbjG107-8__2SM_od9xlA</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2408204344</pqid></control><display><type>article</type><title>Pd-Catalyzed Dearomative Asymmetric Allylic Alkylation of Naphthols with Alkoxyallenes</title><source>American Chemical Society</source><creator>Hu, Jinjin ; Pan, Shulei ; Zhu, Shuai ; Yu, Peiyuan ; Xu, Ruigang ; Zhong, Guofu ; Zeng, Xiaofei</creator><creatorcontrib>Hu, Jinjin ; Pan, Shulei ; Zhu, Shuai ; Yu, Peiyuan ; Xu, Ruigang ; Zhong, Guofu ; Zeng, Xiaofei</creatorcontrib><description>An Pd-catalyzed linear selective intermolecular asymmetric dearomative allylic alkylation reaction of naphthols with alkoxyallenes under mild reaction conditions is reported. The transformation is successfully promoted by Pd2(dba)3 and chiral Trost ligand, and provides a general atom-efficient protocol to obtain various β-naphthalenones bearing an all carbon quaternary stereogenic center in good yields, chemo- and stereoselectivities.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.0c00582</identifier><identifier>PMID: 32466648</identifier><language>eng</language><publisher>United States</publisher><ispartof>Journal of organic chemistry, 2020-06, Vol.85 (12), p.7896-7904</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c297t-7d1b3413bd23948bb930c90828d977a530ab6df7885b8d6eabf93706c4536a553</citedby><cites>FETCH-LOGICAL-c297t-7d1b3413bd23948bb930c90828d977a530ab6df7885b8d6eabf93706c4536a553</cites><orcidid>0000-0002-4367-6866 ; 0000-0003-4222-1365 ; 0000-0001-9497-9069</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,777,781,2752,27905,27906</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/32466648$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Hu, Jinjin</creatorcontrib><creatorcontrib>Pan, Shulei</creatorcontrib><creatorcontrib>Zhu, Shuai</creatorcontrib><creatorcontrib>Yu, Peiyuan</creatorcontrib><creatorcontrib>Xu, Ruigang</creatorcontrib><creatorcontrib>Zhong, Guofu</creatorcontrib><creatorcontrib>Zeng, Xiaofei</creatorcontrib><title>Pd-Catalyzed Dearomative Asymmetric Allylic Alkylation of Naphthols with Alkoxyallenes</title><title>Journal of organic chemistry</title><addtitle>J Org Chem</addtitle><description>An Pd-catalyzed linear selective intermolecular asymmetric dearomative allylic alkylation reaction of naphthols with alkoxyallenes under mild reaction conditions is reported. The transformation is successfully promoted by Pd2(dba)3 and chiral Trost ligand, and provides a general atom-efficient protocol to obtain various β-naphthalenones bearing an all carbon quaternary stereogenic center in good yields, chemo- and stereoselectivities.</description><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNo9kDtPwzAUhS0EoqUws6GMLGlv_IozVuUpVcAArJZfUVOcusQpEH49KS3c5Qznu2f4EDrPYJwBzibKxPEymDEYACbwARpmDEPKC6CHaAiAcUowJwN0EuMS-mOMHaMBwZRzTsUQvT7ZdKZa5btvZ5Mrp5pQq7b6cMk0dnXt2qYyydT7zv_mW-f7NqySUCYPar1oF8HH5LNqF9syfHXKe7dy8RQdlcpHd7bPEXq5uX6e3aXzx9v72XSeGlzkbZrbTBOaEW0xKajQuiBgChBY2CLPFSOgNLdlLgTTwnKndFmQHLihjHDFGBmhy93uugnvGxdbWVfROO_VyoVNlJj2Y0AJpT062aGmCTE2rpTrpqpV08kM5Fam7GXKXqbcy-w_LvbjG107-8__2SM_od9xlA</recordid><startdate>20200619</startdate><enddate>20200619</enddate><creator>Hu, Jinjin</creator><creator>Pan, Shulei</creator><creator>Zhu, Shuai</creator><creator>Yu, Peiyuan</creator><creator>Xu, Ruigang</creator><creator>Zhong, Guofu</creator><creator>Zeng, Xiaofei</creator><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-4367-6866</orcidid><orcidid>https://orcid.org/0000-0003-4222-1365</orcidid><orcidid>https://orcid.org/0000-0001-9497-9069</orcidid></search><sort><creationdate>20200619</creationdate><title>Pd-Catalyzed Dearomative Asymmetric Allylic Alkylation of Naphthols with Alkoxyallenes</title><author>Hu, Jinjin ; Pan, Shulei ; Zhu, Shuai ; Yu, Peiyuan ; Xu, Ruigang ; Zhong, Guofu ; Zeng, Xiaofei</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c297t-7d1b3413bd23948bb930c90828d977a530ab6df7885b8d6eabf93706c4536a553</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hu, Jinjin</creatorcontrib><creatorcontrib>Pan, Shulei</creatorcontrib><creatorcontrib>Zhu, Shuai</creatorcontrib><creatorcontrib>Yu, Peiyuan</creatorcontrib><creatorcontrib>Xu, Ruigang</creatorcontrib><creatorcontrib>Zhong, Guofu</creatorcontrib><creatorcontrib>Zeng, Xiaofei</creatorcontrib><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>Hu, Jinjin</au><au>Pan, Shulei</au><au>Zhu, Shuai</au><au>Yu, Peiyuan</au><au>Xu, Ruigang</au><au>Zhong, Guofu</au><au>Zeng, Xiaofei</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Pd-Catalyzed Dearomative Asymmetric Allylic Alkylation of Naphthols with Alkoxyallenes</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J Org Chem</addtitle><date>2020-06-19</date><risdate>2020</risdate><volume>85</volume><issue>12</issue><spage>7896</spage><epage>7904</epage><pages>7896-7904</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>An Pd-catalyzed linear selective intermolecular asymmetric dearomative allylic alkylation reaction of naphthols with alkoxyallenes under mild reaction conditions is reported. The transformation is successfully promoted by Pd2(dba)3 and chiral Trost ligand, and provides a general atom-efficient protocol to obtain various β-naphthalenones bearing an all carbon quaternary stereogenic center in good yields, chemo- and stereoselectivities.</abstract><cop>United States</cop><pmid>32466648</pmid><doi>10.1021/acs.joc.0c00582</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0002-4367-6866</orcidid><orcidid>https://orcid.org/0000-0003-4222-1365</orcidid><orcidid>https://orcid.org/0000-0001-9497-9069</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 0022-3263
ispartof Journal of organic chemistry, 2020-06, Vol.85 (12), p.7896-7904
issn 0022-3263
1520-6904
language eng
recordid cdi_proquest_miscellaneous_2408204344
source American Chemical Society
title Pd-Catalyzed Dearomative Asymmetric Allylic Alkylation of Naphthols with Alkoxyallenes
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-17T18%3A00%3A55IST&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=Pd-Catalyzed%20Dearomative%20Asymmetric%20Allylic%20Alkylation%20of%20Naphthols%20with%20Alkoxyallenes&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Hu,%20Jinjin&rft.date=2020-06-19&rft.volume=85&rft.issue=12&rft.spage=7896&rft.epage=7904&rft.pages=7896-7904&rft.issn=0022-3263&rft.eissn=1520-6904&rft_id=info:doi/10.1021/acs.joc.0c00582&rft_dat=%3Cproquest_cross%3E2408204344%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=2408204344&rft_id=info:pmid/32466648&rfr_iscdi=true