Asymmetric Double Oxidative [3 + 2] Cycloaddition for the Synthesis of CF3‑Containing Spiro[pyrrolidin-3,2′-oxindole]

An asymmetric double oxidative [3 + 2] cycloaddition is reported. Oxidation of 3-((2,2,2-trifluoroethyl)amino)indolin-2-ones and β-aryl-substituted aldehydes simultaneously and subsequent asymmetric cycloaddition in the presence of the chiral amino catalyst generated highly functionalized chiral C...

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Organic letters 2023-05, Vol.25 (17), p.3152-3156
Hauptverfasser:	Wang, Tao, Wang, Wen-Bin, Fu, Yan-Ming, Zhu, Cheng-Feng, Cheng, Lan-Jun, You, Yang-En, Wu, Xiang, Li, You-Gui
Format:	Artikel
Sprache:	eng
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

container_end_page	3156
container_issue	17
container_start_page	3152
container_title	Organic letters
container_volume	25
creator	Wang, Tao Wang, Wen-Bin Fu, Yan-Ming Zhu, Cheng-Feng Cheng, Lan-Jun You, Yang-En Wu, Xiang Li, You-Gui
description	An asymmetric double oxidative [3 + 2] cycloaddition is reported. Oxidation of 3-((2,2,2-trifluoroethyl)amino)indolin-2-ones and β-aryl-substituted aldehydes simultaneously and subsequent asymmetric cycloaddition in the presence of the chiral amino catalyst generated highly functionalized chiral CF3-containing spiro[pyrrolidin-3,2′-oxindole] with four contiguous stereocenters stereoselectively, which is characterized by directly constructing two C–C bonds from four C(sp3)–H bonds. This new method features mild conditions, broad substrate scope, and excellent functional group compatibility.
doi_str_mv	10.1021/acs.orglett.3c01083
format	Article
fullrecord	<record><control><sourceid>proquest_acs_j</sourceid><recordid>TN_cdi_proquest_miscellaneous_2805031328</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2805031328</sourcerecordid><originalsourceid>FETCH-LOGICAL-a228t-f26d18957af0c93b1a9fe066aef5651c62c9fde11434a070cbe8ba440234911c3</originalsourceid><addsrcrecordid>eNo9kM1KAzEAhIMoWKtP4CVHQbfNz-5291hWq0Khh-qplCWbTWpKmtQkK91bX8FX8ZH6JK60eJphGIbhA-AWowFGBA8Z9wPrVlqEMKAcYZTRM9DDCaHRCCXk_N-n6BJceb9GCHdJ3gPt2LebjQhOcfhom0oLONupmgX1JeCCwntIlrBoubasrlVQ1kBpHQwfAs5b04lXHloJiwk97L8LawJTRpkVnG-Vs4tt65zVqlYmog_ksP-J7E6Z2mqxvAYXkmkvbk7aB--Tp7fiJZrOnl-L8TRihGQhkiStcZYnIyYRz2mFWS4FSlMmZJImmKeE57IWGMc0ZmiEeCWyisUxIjTOMea0D-6Ou1tnPxvhQ7lRngutmRG28SXJUIIopiTrqsNjteNZrm3jTHesxKj8g1z-hSfI5Qky_QX7inVW</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2805031328</pqid></control><display><type>article</type><title>Asymmetric Double Oxidative [3 + 2] Cycloaddition for the Synthesis of CF3‑Containing Spiro[pyrrolidin-3,2′-oxindole]</title><source>American Chemical Society Journals</source><creator>Wang, Tao ; Wang, Wen-Bin ; Fu, Yan-Ming ; Zhu, Cheng-Feng ; Cheng, Lan-Jun ; You, Yang-En ; Wu, Xiang ; Li, You-Gui</creator><creatorcontrib>Wang, Tao ; Wang, Wen-Bin ; Fu, Yan-Ming ; Zhu, Cheng-Feng ; Cheng, Lan-Jun ; You, Yang-En ; Wu, Xiang ; Li, You-Gui</creatorcontrib><description>An asymmetric double oxidative [3 + 2] cycloaddition is reported. Oxidation of 3-((2,2,2-trifluoroethyl)amino)indolin-2-ones and β-aryl-substituted aldehydes simultaneously and subsequent asymmetric cycloaddition in the presence of the chiral amino catalyst generated highly functionalized chiral CF3-containing spiro[pyrrolidin-3,2′-oxindole] with four contiguous stereocenters stereoselectively, which is characterized by directly constructing two C–C bonds from four C(sp3)–H bonds. This new method features mild conditions, broad substrate scope, and excellent functional group compatibility.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.3c01083</identifier><language>eng</language><publisher>American Chemical Society</publisher><ispartof>Organic letters, 2023-05, Vol.25 (17), p.3152-3156</ispartof><rights>2023 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><orcidid>0000-0001-5428-9063 ; 0000-0002-9676-6750</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.orglett.3c01083$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.orglett.3c01083$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,27053,27901,27902,56713,56763</link.rule.ids></links><search><creatorcontrib>Wang, Tao</creatorcontrib><creatorcontrib>Wang, Wen-Bin</creatorcontrib><creatorcontrib>Fu, Yan-Ming</creatorcontrib><creatorcontrib>Zhu, Cheng-Feng</creatorcontrib><creatorcontrib>Cheng, Lan-Jun</creatorcontrib><creatorcontrib>You, Yang-En</creatorcontrib><creatorcontrib>Wu, Xiang</creatorcontrib><creatorcontrib>Li, You-Gui</creatorcontrib><title>Asymmetric Double Oxidative [3 + 2] Cycloaddition for the Synthesis of CF3‑Containing Spiro[pyrrolidin-3,2′-oxindole]</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>An asymmetric double oxidative [3 + 2] cycloaddition is reported. Oxidation of 3-((2,2,2-trifluoroethyl)amino)indolin-2-ones and β-aryl-substituted aldehydes simultaneously and subsequent asymmetric cycloaddition in the presence of the chiral amino catalyst generated highly functionalized chiral CF3-containing spiro[pyrrolidin-3,2′-oxindole] with four contiguous stereocenters stereoselectively, which is characterized by directly constructing two C–C bonds from four C(sp3)–H bonds. This new method features mild conditions, broad substrate scope, and excellent functional group compatibility.</description><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNo9kM1KAzEAhIMoWKtP4CVHQbfNz-5291hWq0Khh-qplCWbTWpKmtQkK91bX8FX8ZH6JK60eJphGIbhA-AWowFGBA8Z9wPrVlqEMKAcYZTRM9DDCaHRCCXk_N-n6BJceb9GCHdJ3gPt2LebjQhOcfhom0oLONupmgX1JeCCwntIlrBoubasrlVQ1kBpHQwfAs5b04lXHloJiwk97L8LawJTRpkVnG-Vs4tt65zVqlYmog_ksP-J7E6Z2mqxvAYXkmkvbk7aB--Tp7fiJZrOnl-L8TRihGQhkiStcZYnIyYRz2mFWS4FSlMmZJImmKeE57IWGMc0ZmiEeCWyisUxIjTOMea0D-6Ou1tnPxvhQ7lRngutmRG28SXJUIIopiTrqsNjteNZrm3jTHesxKj8g1z-hSfI5Qky_QX7inVW</recordid><startdate>20230505</startdate><enddate>20230505</enddate><creator>Wang, Tao</creator><creator>Wang, Wen-Bin</creator><creator>Fu, Yan-Ming</creator><creator>Zhu, Cheng-Feng</creator><creator>Cheng, Lan-Jun</creator><creator>You, Yang-En</creator><creator>Wu, Xiang</creator><creator>Li, You-Gui</creator><general>American Chemical Society</general><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-5428-9063</orcidid><orcidid>https://orcid.org/0000-0002-9676-6750</orcidid></search><sort><creationdate>20230505</creationdate><title>Asymmetric Double Oxidative [3 + 2] Cycloaddition for the Synthesis of CF3‑Containing Spiro[pyrrolidin-3,2′-oxindole]</title><author>Wang, Tao ; Wang, Wen-Bin ; Fu, Yan-Ming ; Zhu, Cheng-Feng ; Cheng, Lan-Jun ; You, Yang-En ; Wu, Xiang ; Li, You-Gui</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a228t-f26d18957af0c93b1a9fe066aef5651c62c9fde11434a070cbe8ba440234911c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wang, Tao</creatorcontrib><creatorcontrib>Wang, Wen-Bin</creatorcontrib><creatorcontrib>Fu, Yan-Ming</creatorcontrib><creatorcontrib>Zhu, Cheng-Feng</creatorcontrib><creatorcontrib>Cheng, Lan-Jun</creatorcontrib><creatorcontrib>You, Yang-En</creatorcontrib><creatorcontrib>Wu, Xiang</creatorcontrib><creatorcontrib>Li, You-Gui</creatorcontrib><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wang, Tao</au><au>Wang, Wen-Bin</au><au>Fu, Yan-Ming</au><au>Zhu, Cheng-Feng</au><au>Cheng, Lan-Jun</au><au>You, Yang-En</au><au>Wu, Xiang</au><au>Li, You-Gui</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Asymmetric Double Oxidative [3 + 2] Cycloaddition for the Synthesis of CF3‑Containing Spiro[pyrrolidin-3,2′-oxindole]</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2023-05-05</date><risdate>2023</risdate><volume>25</volume><issue>17</issue><spage>3152</spage><epage>3156</epage><pages>3152-3156</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>An asymmetric double oxidative [3 + 2] cycloaddition is reported. Oxidation of 3-((2,2,2-trifluoroethyl)amino)indolin-2-ones and β-aryl-substituted aldehydes simultaneously and subsequent asymmetric cycloaddition in the presence of the chiral amino catalyst generated highly functionalized chiral CF3-containing spiro[pyrrolidin-3,2′-oxindole] with four contiguous stereocenters stereoselectively, which is characterized by directly constructing two C–C bonds from four C(sp3)–H bonds. This new method features mild conditions, broad substrate scope, and excellent functional group compatibility.</abstract><pub>American Chemical Society</pub><doi>10.1021/acs.orglett.3c01083</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0001-5428-9063</orcidid><orcidid>https://orcid.org/0000-0002-9676-6750</orcidid></addata></record>
fulltext	fulltext
identifier	ISSN: 1523-7060
ispartof	Organic letters, 2023-05, Vol.25 (17), p.3152-3156
issn	1523-7060 1523-7052
language	eng
recordid	cdi_proquest_miscellaneous_2805031328
source	American Chemical Society Journals
title	Asymmetric Double Oxidative [3 + 2] Cycloaddition for the Synthesis of CF3‑Containing Spiro[pyrrolidin-3,2′-oxindole]
url	https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-04T05%3A44%3A44IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_acs_j&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Asymmetric%20Double%20Oxidative%20%5B3%20+%202%5D%20Cycloaddition%20for%20the%20Synthesis%20of%20CF3%E2%80%91Containing%20Spiro%5Bpyrrolidin-3,2%E2%80%B2-oxindole%5D&rft.jtitle=Organic%20letters&rft.au=Wang,%20Tao&rft.date=2023-05-05&rft.volume=25&rft.issue=17&rft.spage=3152&rft.epage=3156&rft.pages=3152-3156&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/acs.orglett.3c01083&rft_dat=%3Cproquest_acs_j%3E2805031328%3C/proquest_acs_j%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2805031328&rft_id=info:pmid/&rfr_iscdi=true