Enantioselective Synthesis of Spiroketals and Spiroaminals via Gold and Iridium Sequential Catalysis
The enantioselective cascade reaction between racemic 2‐(1‐hydroxyallyl)phenols and alkynols/alkynamides was realized by using a gold and iridium sequential catalytic system. In this procedure, the in situ generated exocyclic vinyl ethers or enamides undergo the asymmetric allylation/spiroketalizati...
Gespeichert in:
Veröffentlicht in: | Angewandte Chemie International Edition 2022-06, Vol.61 (26), p.e202203661-n/a |
---|---|
Hauptverfasser: | , , , |
Format: | Artikel |
Sprache: | eng |
Schlagworte: | |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
container_end_page | n/a |
---|---|
container_issue | 26 |
container_start_page | e202203661 |
container_title | Angewandte Chemie International Edition |
container_volume | 61 |
creator | Yang, Wu‐Lin Shang, Xin‐Yu Luo, Xiaoyan Deng, Wei‐Ping |
description | The enantioselective cascade reaction between racemic 2‐(1‐hydroxyallyl)phenols and alkynols/alkynamides was realized by using a gold and iridium sequential catalytic system. In this procedure, the in situ generated exocyclic vinyl ethers or enamides undergo the asymmetric allylation/spiroketalization with π‐ally‐Ir amphiphilic species, which provides an efficient and straightforward access to spiroketals and spiroaminals with excellent enantioselectivities. Moreover, racemic 2‐(1‐hydroxyallyl)anilines were also suitable in this reaction along with a kinetic resolution process, affording enantioenriched spiroaminals and 2‐(1‐hydroxyallyl)anilines in good yields. The synthetic utility of this method has been demonstrated by efficient enantioselective synthesis of the analogue of Paecilospirone.
An asymmetric cascade reaction of 2‐(1‐hydroxyallyl)phenols/2‐(1‐hydroxyallyl)anilines with alkynyl alcohols/amides was realized by using a novel Au/Ir sequential catalytic system, which enables the facile synthesis of structurally diverse spiroketals and spiroaminals with up to high diastereoselectivities and excellent enantioselectivities. |
doi_str_mv | 10.1002/anie.202203661 |
format | Article |
fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2653269966</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2653269966</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3031-42df534341822b3a44b889e5787d93489fe1f19224b3fa94573cd33e9714a1703</originalsourceid><addsrcrecordid>eNqFkM1PwjAYhxujEUSvHs0SL16Gbd9ubY-EIJIQPaDnpWzvYnEfuG4Y_nuLICZePPXr-T15-yPkmtEho5Tfm8rikFPOKcQxOyF9FnEWgpRw6vcCIJQqYj1y4dzK80rR-Jz0IBIiFpL3STapTNXa2mGBaWs3GCy2VfuGzrqgzoPF2jb1O7amcIGpsv3ZlLbaXWysCaZ1kX2_zBqb2a4MFvjRoTeaIhgbn9t60yU5y30Arw7rgLw-TF7Gj-H8eTobj-ZhChRYKHiWRyBAMMX5EowQS6U0RlLJTINQOkeWM825WEJutIgkpBkAasmEYZLCgNztveum9lO4NimtS7EoTIV15xIeR8BjrePYo7d_0FXdNbtveUoqj_mKPDXcU2lTO9dgnqwbW5pmmzCa7PpPdv0nx_594Oag7ZYlZkf8p3AP6D3waQvc_qNLRk-zya_8C1BhkMs</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2678326544</pqid></control><display><type>article</type><title>Enantioselective Synthesis of Spiroketals and Spiroaminals via Gold and Iridium Sequential Catalysis</title><source>Access via Wiley Online Library</source><creator>Yang, Wu‐Lin ; Shang, Xin‐Yu ; Luo, Xiaoyan ; Deng, Wei‐Ping</creator><creatorcontrib>Yang, Wu‐Lin ; Shang, Xin‐Yu ; Luo, Xiaoyan ; Deng, Wei‐Ping</creatorcontrib><description>The enantioselective cascade reaction between racemic 2‐(1‐hydroxyallyl)phenols and alkynols/alkynamides was realized by using a gold and iridium sequential catalytic system. In this procedure, the in situ generated exocyclic vinyl ethers or enamides undergo the asymmetric allylation/spiroketalization with π‐ally‐Ir amphiphilic species, which provides an efficient and straightforward access to spiroketals and spiroaminals with excellent enantioselectivities. Moreover, racemic 2‐(1‐hydroxyallyl)anilines were also suitable in this reaction along with a kinetic resolution process, affording enantioenriched spiroaminals and 2‐(1‐hydroxyallyl)anilines in good yields. The synthetic utility of this method has been demonstrated by efficient enantioselective synthesis of the analogue of Paecilospirone.
An asymmetric cascade reaction of 2‐(1‐hydroxyallyl)phenols/2‐(1‐hydroxyallyl)anilines with alkynyl alcohols/amides was realized by using a novel Au/Ir sequential catalytic system, which enables the facile synthesis of structurally diverse spiroketals and spiroaminals with up to high diastereoselectivities and excellent enantioselectivities.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.202203661</identifier><identifier>PMID: 35446472</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Allyl compounds ; Allylation ; Aniline ; Asymmetric Synthesis ; Cascade chemical reactions ; Cascade Reactions ; Catalysis ; Chemical reactions ; Enantiomers ; Ethers ; Gold ; Iridium ; Phenols ; Sequential Catalysis ; Spiroketals/Spiroaminals ; Vinyl ethers</subject><ispartof>Angewandte Chemie International Edition, 2022-06, Vol.61 (26), p.e202203661-n/a</ispartof><rights>2022 Wiley‐VCH GmbH</rights><rights>2022 Wiley-VCH GmbH.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3031-42df534341822b3a44b889e5787d93489fe1f19224b3fa94573cd33e9714a1703</citedby><cites>FETCH-LOGICAL-c3031-42df534341822b3a44b889e5787d93489fe1f19224b3fa94573cd33e9714a1703</cites><orcidid>0000-0001-7985-5017</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fanie.202203661$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.202203661$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/35446472$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Yang, Wu‐Lin</creatorcontrib><creatorcontrib>Shang, Xin‐Yu</creatorcontrib><creatorcontrib>Luo, Xiaoyan</creatorcontrib><creatorcontrib>Deng, Wei‐Ping</creatorcontrib><title>Enantioselective Synthesis of Spiroketals and Spiroaminals via Gold and Iridium Sequential Catalysis</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>The enantioselective cascade reaction between racemic 2‐(1‐hydroxyallyl)phenols and alkynols/alkynamides was realized by using a gold and iridium sequential catalytic system. In this procedure, the in situ generated exocyclic vinyl ethers or enamides undergo the asymmetric allylation/spiroketalization with π‐ally‐Ir amphiphilic species, which provides an efficient and straightforward access to spiroketals and spiroaminals with excellent enantioselectivities. Moreover, racemic 2‐(1‐hydroxyallyl)anilines were also suitable in this reaction along with a kinetic resolution process, affording enantioenriched spiroaminals and 2‐(1‐hydroxyallyl)anilines in good yields. The synthetic utility of this method has been demonstrated by efficient enantioselective synthesis of the analogue of Paecilospirone.
An asymmetric cascade reaction of 2‐(1‐hydroxyallyl)phenols/2‐(1‐hydroxyallyl)anilines with alkynyl alcohols/amides was realized by using a novel Au/Ir sequential catalytic system, which enables the facile synthesis of structurally diverse spiroketals and spiroaminals with up to high diastereoselectivities and excellent enantioselectivities.</description><subject>Allyl compounds</subject><subject>Allylation</subject><subject>Aniline</subject><subject>Asymmetric Synthesis</subject><subject>Cascade chemical reactions</subject><subject>Cascade Reactions</subject><subject>Catalysis</subject><subject>Chemical reactions</subject><subject>Enantiomers</subject><subject>Ethers</subject><subject>Gold</subject><subject>Iridium</subject><subject>Phenols</subject><subject>Sequential Catalysis</subject><subject>Spiroketals/Spiroaminals</subject><subject>Vinyl ethers</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNqFkM1PwjAYhxujEUSvHs0SL16Gbd9ubY-EIJIQPaDnpWzvYnEfuG4Y_nuLICZePPXr-T15-yPkmtEho5Tfm8rikFPOKcQxOyF9FnEWgpRw6vcCIJQqYj1y4dzK80rR-Jz0IBIiFpL3STapTNXa2mGBaWs3GCy2VfuGzrqgzoPF2jb1O7amcIGpsv3ZlLbaXWysCaZ1kX2_zBqb2a4MFvjRoTeaIhgbn9t60yU5y30Arw7rgLw-TF7Gj-H8eTobj-ZhChRYKHiWRyBAMMX5EowQS6U0RlLJTINQOkeWM825WEJutIgkpBkAasmEYZLCgNztveum9lO4NimtS7EoTIV15xIeR8BjrePYo7d_0FXdNbtveUoqj_mKPDXcU2lTO9dgnqwbW5pmmzCa7PpPdv0nx_594Oag7ZYlZkf8p3AP6D3waQvc_qNLRk-zya_8C1BhkMs</recordid><startdate>20220627</startdate><enddate>20220627</enddate><creator>Yang, Wu‐Lin</creator><creator>Shang, Xin‐Yu</creator><creator>Luo, Xiaoyan</creator><creator>Deng, Wei‐Ping</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-7985-5017</orcidid></search><sort><creationdate>20220627</creationdate><title>Enantioselective Synthesis of Spiroketals and Spiroaminals via Gold and Iridium Sequential Catalysis</title><author>Yang, Wu‐Lin ; Shang, Xin‐Yu ; Luo, Xiaoyan ; Deng, Wei‐Ping</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3031-42df534341822b3a44b889e5787d93489fe1f19224b3fa94573cd33e9714a1703</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Allyl compounds</topic><topic>Allylation</topic><topic>Aniline</topic><topic>Asymmetric Synthesis</topic><topic>Cascade chemical reactions</topic><topic>Cascade Reactions</topic><topic>Catalysis</topic><topic>Chemical reactions</topic><topic>Enantiomers</topic><topic>Ethers</topic><topic>Gold</topic><topic>Iridium</topic><topic>Phenols</topic><topic>Sequential Catalysis</topic><topic>Spiroketals/Spiroaminals</topic><topic>Vinyl ethers</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yang, Wu‐Lin</creatorcontrib><creatorcontrib>Shang, Xin‐Yu</creatorcontrib><creatorcontrib>Luo, Xiaoyan</creatorcontrib><creatorcontrib>Deng, Wei‐Ping</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yang, Wu‐Lin</au><au>Shang, Xin‐Yu</au><au>Luo, Xiaoyan</au><au>Deng, Wei‐Ping</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enantioselective Synthesis of Spiroketals and Spiroaminals via Gold and Iridium Sequential Catalysis</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2022-06-27</date><risdate>2022</risdate><volume>61</volume><issue>26</issue><spage>e202203661</spage><epage>n/a</epage><pages>e202203661-n/a</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>The enantioselective cascade reaction between racemic 2‐(1‐hydroxyallyl)phenols and alkynols/alkynamides was realized by using a gold and iridium sequential catalytic system. In this procedure, the in situ generated exocyclic vinyl ethers or enamides undergo the asymmetric allylation/spiroketalization with π‐ally‐Ir amphiphilic species, which provides an efficient and straightforward access to spiroketals and spiroaminals with excellent enantioselectivities. Moreover, racemic 2‐(1‐hydroxyallyl)anilines were also suitable in this reaction along with a kinetic resolution process, affording enantioenriched spiroaminals and 2‐(1‐hydroxyallyl)anilines in good yields. The synthetic utility of this method has been demonstrated by efficient enantioselective synthesis of the analogue of Paecilospirone.
An asymmetric cascade reaction of 2‐(1‐hydroxyallyl)phenols/2‐(1‐hydroxyallyl)anilines with alkynyl alcohols/amides was realized by using a novel Au/Ir sequential catalytic system, which enables the facile synthesis of structurally diverse spiroketals and spiroaminals with up to high diastereoselectivities and excellent enantioselectivities.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>35446472</pmid><doi>10.1002/anie.202203661</doi><tpages>6</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0001-7985-5017</orcidid></addata></record> |
fulltext | fulltext |
identifier | ISSN: 1433-7851 |
ispartof | Angewandte Chemie International Edition, 2022-06, Vol.61 (26), p.e202203661-n/a |
issn | 1433-7851 1521-3773 |
language | eng |
recordid | cdi_proquest_miscellaneous_2653269966 |
source | Access via Wiley Online Library |
subjects | Allyl compounds Allylation Aniline Asymmetric Synthesis Cascade chemical reactions Cascade Reactions Catalysis Chemical reactions Enantiomers Ethers Gold Iridium Phenols Sequential Catalysis Spiroketals/Spiroaminals Vinyl ethers |
title | Enantioselective Synthesis of Spiroketals and Spiroaminals via Gold and Iridium Sequential Catalysis |
url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-23T14%3A23%3A28IST&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%20Synthesis%20of%20Spiroketals%20and%20Spiroaminals%20via%20Gold%20and%20Iridium%20Sequential%20Catalysis&rft.jtitle=Angewandte%20Chemie%20International%20Edition&rft.au=Yang,%20Wu%E2%80%90Lin&rft.date=2022-06-27&rft.volume=61&rft.issue=26&rft.spage=e202203661&rft.epage=n/a&rft.pages=e202203661-n/a&rft.issn=1433-7851&rft.eissn=1521-3773&rft_id=info:doi/10.1002/anie.202203661&rft_dat=%3Cproquest_cross%3E2653269966%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=2678326544&rft_id=info:pmid/35446472&rfr_iscdi=true |