Chiral Lewis Base/Achiral Acid Co‐Catalyzed Atroposelective Sulfenylation of Pyrrole Derivatives: Construction of C—N Axially Chiral Sulfides
Comprehensive Summary Chiral BINAM‐derived selenide/achiral acid co‐catalyzed atroposelective electrophilic sulfenylation of pyrrole derivatives has been realized for the first time. A variety of C—N axially chiral sulfur‐containing pyrrole derivatives were readily obtained in moderate to good yield...
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| Veröffentlicht in: | Chinese journal of chemistry 2024-09, Vol.42 (17), p.2005-2009 |
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| Hauptverfasser: | , , , , , |
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| container_end_page | 2009 |
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| container_issue | 17 |
| container_start_page | 2005 |
| container_title | Chinese journal of chemistry |
| container_volume | 42 |
| creator | Yang, Qin Luo, Hui‐Yun Zhu, Deng Zhang, Xin‐Yu Ke, Hua Chen, Zhi‐Min |
| description | Comprehensive Summary
Chiral BINAM‐derived selenide/achiral acid co‐catalyzed atroposelective electrophilic sulfenylation of pyrrole derivatives has been realized for the first time. A variety of C—N axially chiral sulfur‐containing pyrrole derivatives were readily obtained in moderate to good yields with moderate to excellent enantioselectivities. This catalytic system involves sequential desymmetrization and kinetic resolution.
Chiral BINAM‐derived selenide/achiral acid co‐catalyzed atroposelective electrophilic sulfenylation of pyrrole derivatives has been realized for the first time. |
| doi_str_mv | 10.1002/cjoc.202400255 |
| format | Article |
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Chiral BINAM‐derived selenide/achiral acid co‐catalyzed atroposelective electrophilic sulfenylation of pyrrole derivatives has been realized for the first time. A variety of C—N axially chiral sulfur‐containing pyrrole derivatives were readily obtained in moderate to good yields with moderate to excellent enantioselectivities. This catalytic system involves sequential desymmetrization and kinetic resolution.
Chiral BINAM‐derived selenide/achiral acid co‐catalyzed atroposelective electrophilic sulfenylation of pyrrole derivatives has been realized for the first time.</description><identifier>ISSN: 1001-604X</identifier><identifier>EISSN: 1614-7065</identifier><identifier>DOI: 10.1002/cjoc.202400255</identifier><language>eng</language><publisher>Weinheim: WILEY‐VCH Verlag GmbH & Co. KGaA</publisher><subject>Asymmetric catalysis ; Atropisomerism ; Desymmetrization ; Electrophilic substitution ; Heterocycles ; Kinetic resolution ; Lewis base ; Selenide ; Sulfur</subject><ispartof>Chinese journal of chemistry, 2024-09, Vol.42 (17), p.2005-2009</ispartof><rights>2024 SIOC, CAS, Shanghai, & WILEY‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c2725-9d4fa22424eed5b164f4cc2c7eb61f2730e81409130eba69c66810c8ab7f58043</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fcjoc.202400255$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fcjoc.202400255$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Yang, Qin</creatorcontrib><creatorcontrib>Luo, Hui‐Yun</creatorcontrib><creatorcontrib>Zhu, Deng</creatorcontrib><creatorcontrib>Zhang, Xin‐Yu</creatorcontrib><creatorcontrib>Ke, Hua</creatorcontrib><creatorcontrib>Chen, Zhi‐Min</creatorcontrib><title>Chiral Lewis Base/Achiral Acid Co‐Catalyzed Atroposelective Sulfenylation of Pyrrole Derivatives: Construction of C—N Axially Chiral Sulfides</title><title>Chinese journal of chemistry</title><description>Comprehensive Summary
Chiral BINAM‐derived selenide/achiral acid co‐catalyzed atroposelective electrophilic sulfenylation of pyrrole derivatives has been realized for the first time. A variety of C—N axially chiral sulfur‐containing pyrrole derivatives were readily obtained in moderate to good yields with moderate to excellent enantioselectivities. This catalytic system involves sequential desymmetrization and kinetic resolution.
Chiral BINAM‐derived selenide/achiral acid co‐catalyzed atroposelective electrophilic sulfenylation of pyrrole derivatives has been realized for the first time.</description><subject>Asymmetric catalysis</subject><subject>Atropisomerism</subject><subject>Desymmetrization</subject><subject>Electrophilic substitution</subject><subject>Heterocycles</subject><subject>Kinetic resolution</subject><subject>Lewis base</subject><subject>Selenide</subject><subject>Sulfur</subject><issn>1001-604X</issn><issn>1614-7065</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNqFkL1OwzAUhSMEEqWwMltiTmu7jpOwhfCviiIBElvkODfClamLnVLC1EcAiSfsk5AoBUam-6PvnHt1PO-Q4AHBmA7l1MgBxZQ1QxBseT3CCfNDzIPtpseY-Byzx11vz7lpg4Qh5T3vM31SVmg0hqVy6EQ4GCayWyVSFSg169VHKiqh63coUFJZMzcONMhKvQK6W-gSZrUWlTIzZEp0W1trNKBTsOpVtIw7bkxmrrIL-QOl69XXDUrelNC6RpsPWitVgNv3dkqhHRxsat97OD-7Ty_98eTiKk3GvqQhDfy4YKWglFEGUAQ54axkUlIZQs5JScMRhogwHJOmyQWPJecRwTISeVgGEWajvnfU-c6teVmAq7KpWdhZczIb4YiHcYBJ3FCDjpLWOGehzOZWPQtbZwRnbexZG3v2G3sjiDvBUmmo_6Gz9HqS_mm_AZTiii8</recordid><startdate>20240901</startdate><enddate>20240901</enddate><creator>Yang, Qin</creator><creator>Luo, Hui‐Yun</creator><creator>Zhu, Deng</creator><creator>Zhang, Xin‐Yu</creator><creator>Ke, Hua</creator><creator>Chen, Zhi‐Min</creator><general>WILEY‐VCH Verlag GmbH & Co. KGaA</general><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20240901</creationdate><title>Chiral Lewis Base/Achiral Acid Co‐Catalyzed Atroposelective Sulfenylation of Pyrrole Derivatives: Construction of C—N Axially Chiral Sulfides</title><author>Yang, Qin ; Luo, Hui‐Yun ; Zhu, Deng ; Zhang, Xin‐Yu ; Ke, Hua ; Chen, Zhi‐Min</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2725-9d4fa22424eed5b164f4cc2c7eb61f2730e81409130eba69c66810c8ab7f58043</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Asymmetric catalysis</topic><topic>Atropisomerism</topic><topic>Desymmetrization</topic><topic>Electrophilic substitution</topic><topic>Heterocycles</topic><topic>Kinetic resolution</topic><topic>Lewis base</topic><topic>Selenide</topic><topic>Sulfur</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yang, Qin</creatorcontrib><creatorcontrib>Luo, Hui‐Yun</creatorcontrib><creatorcontrib>Zhu, Deng</creatorcontrib><creatorcontrib>Zhang, Xin‐Yu</creatorcontrib><creatorcontrib>Ke, Hua</creatorcontrib><creatorcontrib>Chen, Zhi‐Min</creatorcontrib><collection>CrossRef</collection><jtitle>Chinese journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yang, Qin</au><au>Luo, Hui‐Yun</au><au>Zhu, Deng</au><au>Zhang, Xin‐Yu</au><au>Ke, Hua</au><au>Chen, Zhi‐Min</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Chiral Lewis Base/Achiral Acid Co‐Catalyzed Atroposelective Sulfenylation of Pyrrole Derivatives: Construction of C—N Axially Chiral Sulfides</atitle><jtitle>Chinese journal of chemistry</jtitle><date>2024-09-01</date><risdate>2024</risdate><volume>42</volume><issue>17</issue><spage>2005</spage><epage>2009</epage><pages>2005-2009</pages><issn>1001-604X</issn><eissn>1614-7065</eissn><abstract>Comprehensive Summary
Chiral BINAM‐derived selenide/achiral acid co‐catalyzed atroposelective electrophilic sulfenylation of pyrrole derivatives has been realized for the first time. A variety of C—N axially chiral sulfur‐containing pyrrole derivatives were readily obtained in moderate to good yields with moderate to excellent enantioselectivities. This catalytic system involves sequential desymmetrization and kinetic resolution.
Chiral BINAM‐derived selenide/achiral acid co‐catalyzed atroposelective electrophilic sulfenylation of pyrrole derivatives has been realized for the first time.</abstract><cop>Weinheim</cop><pub>WILEY‐VCH Verlag GmbH & Co. KGaA</pub><doi>10.1002/cjoc.202400255</doi><tpages>5</tpages></addata></record> |
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| identifier | ISSN: 1001-604X |
| ispartof | Chinese journal of chemistry, 2024-09, Vol.42 (17), p.2005-2009 |
| issn | 1001-604X 1614-7065 |
| language | eng |
| recordid | cdi_proquest_journals_3086795019 |
| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Asymmetric catalysis Atropisomerism Desymmetrization Electrophilic substitution Heterocycles Kinetic resolution Lewis base Selenide Sulfur |
| title | Chiral Lewis Base/Achiral Acid Co‐Catalyzed Atroposelective Sulfenylation of Pyrrole Derivatives: Construction of C—N Axially Chiral Sulfides |
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