Photoinduced carbene transfer for copper-catalyzed asymmetric [4 + 1] cycloadditions: an entry to chiral indolines bearing quaternary stereocenters
Indoline skeletons are widely found in many natural isolates and pharmaceuticals, making indoline synthesis an ongoing research hotspot in synthetic chemistry. However, the catalytic asymmetric de novo construction of indolines bearing chiral quaternary stereocenters remains challenging. Herein, we...
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| Veröffentlicht in: | Organic Chemistry Frontiers 2023-07, Vol.10 (14), p.3498-3503 |
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| creator | Qu, Bao-Le Shi, Bin He, Lin Shi, Jun-Wei Xiao, Wen-Jing Lu, Liang-Qiu |
| description | Indoline skeletons are widely found in many natural isolates and pharmaceuticals, making indoline synthesis an ongoing research hotspot in synthetic chemistry. However, the catalytic asymmetric
de novo
construction of indolines bearing chiral quaternary stereocenters remains challenging. Herein, we present a solution to this unmet challenge through copper-catalyzed asymmetric [4 + 1] cycloadditions of ethynylbenzoxazinones with sulfur ylides, which are formed
in situ
by photoinduced carbene transfer. As a result, a wide range of chiral indolines bearing C2-quaternary stereocenters are obtained with good enantio- and diastereoselectivities (up to 19 : 1 dr and 96 : 4 er). |
| doi_str_mv | 10.1039/D3QO00551H |
| format | Article |
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de novo
construction of indolines bearing chiral quaternary stereocenters remains challenging. Herein, we present a solution to this unmet challenge through copper-catalyzed asymmetric [4 + 1] cycloadditions of ethynylbenzoxazinones with sulfur ylides, which are formed
in situ
by photoinduced carbene transfer. As a result, a wide range of chiral indolines bearing C2-quaternary stereocenters are obtained with good enantio- and diastereoselectivities (up to 19 : 1 dr and 96 : 4 er).</description><identifier>ISSN: 2052-4129</identifier><identifier>ISSN: 2052-4110</identifier><identifier>EISSN: 2052-4129</identifier><identifier>EISSN: 2052-4110</identifier><identifier>DOI: 10.1039/D3QO00551H</identifier><language>eng</language><publisher>London: Royal Society of Chemistry</publisher><subject>Asymmetry ; Carbenes ; Copper ; Heterocyclic compounds ; Organic chemistry ; Sulfur</subject><ispartof>Organic Chemistry Frontiers, 2023-07, Vol.10 (14), p.3498-3503</ispartof><rights>Copyright Royal Society of Chemistry 2023</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c281t-65032cf71b08851fea29a3528f0f5856baca14d8bf0ecdfae739c47877f9d1d3</citedby><cites>FETCH-LOGICAL-c281t-65032cf71b08851fea29a3528f0f5856baca14d8bf0ecdfae739c47877f9d1d3</cites><orcidid>0000-0002-9318-6021 ; 0000-0003-2177-4729</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids></links><search><creatorcontrib>Qu, Bao-Le</creatorcontrib><creatorcontrib>Shi, Bin</creatorcontrib><creatorcontrib>He, Lin</creatorcontrib><creatorcontrib>Shi, Jun-Wei</creatorcontrib><creatorcontrib>Xiao, Wen-Jing</creatorcontrib><creatorcontrib>Lu, Liang-Qiu</creatorcontrib><title>Photoinduced carbene transfer for copper-catalyzed asymmetric [4 + 1] cycloadditions: an entry to chiral indolines bearing quaternary stereocenters</title><title>Organic Chemistry Frontiers</title><description>Indoline skeletons are widely found in many natural isolates and pharmaceuticals, making indoline synthesis an ongoing research hotspot in synthetic chemistry. However, the catalytic asymmetric
de novo
construction of indolines bearing chiral quaternary stereocenters remains challenging. Herein, we present a solution to this unmet challenge through copper-catalyzed asymmetric [4 + 1] cycloadditions of ethynylbenzoxazinones with sulfur ylides, which are formed
in situ
by photoinduced carbene transfer. As a result, a wide range of chiral indolines bearing C2-quaternary stereocenters are obtained with good enantio- and diastereoselectivities (up to 19 : 1 dr and 96 : 4 er).</description><subject>Asymmetry</subject><subject>Carbenes</subject><subject>Copper</subject><subject>Heterocyclic compounds</subject><subject>Organic chemistry</subject><subject>Sulfur</subject><issn>2052-4129</issn><issn>2052-4110</issn><issn>2052-4129</issn><issn>2052-4110</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNpNkE9LAzEQxRdRsNRe_AQBb8pqkt10d71J_VOhUIXeRJbZZGK3bJM2yR7Wr-EXNlJBD8O8w-_NPF6SnDN6zWhW3dxnr0tKhWDzo2TEqeBpznh1_E-fJhPvN5RSxsWUimKUfL2sbbCtUb1ERSS4Bg2S4MB4jY5o64i0ux26VEKAbviMFPhhu8XgWknecnJF2DuRg-wsKNWG1hp_S8AQNMENJFgi162DjsQftmsNetIguNZ8kH0PAZ2BiPko0MroQefPkhMNncfJ7x4nq8eH1WyeLpZPz7O7RSp5yUI6FTTjUhesoWUpmEbgFWSCl5pqUYppAxJYrspGU5RKAxZZJfOiLApdKaaycXJxOLtzdt-jD_XG9jFO52teZiJncapIXR4o6az3DnW9c-02Zq4ZrX9qr_9qz74BQ3d39w</recordid><startdate>20230711</startdate><enddate>20230711</enddate><creator>Qu, Bao-Le</creator><creator>Shi, Bin</creator><creator>He, Lin</creator><creator>Shi, Jun-Wei</creator><creator>Xiao, Wen-Jing</creator><creator>Lu, Liang-Qiu</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>FR3</scope><scope>JG9</scope><scope>P64</scope><orcidid>https://orcid.org/0000-0002-9318-6021</orcidid><orcidid>https://orcid.org/0000-0003-2177-4729</orcidid></search><sort><creationdate>20230711</creationdate><title>Photoinduced carbene transfer for copper-catalyzed asymmetric [4 + 1] cycloadditions: an entry to chiral indolines bearing quaternary stereocenters</title><author>Qu, Bao-Le ; Shi, Bin ; He, Lin ; Shi, Jun-Wei ; Xiao, Wen-Jing ; Lu, Liang-Qiu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c281t-65032cf71b08851fea29a3528f0f5856baca14d8bf0ecdfae739c47877f9d1d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Asymmetry</topic><topic>Carbenes</topic><topic>Copper</topic><topic>Heterocyclic compounds</topic><topic>Organic chemistry</topic><topic>Sulfur</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Qu, Bao-Le</creatorcontrib><creatorcontrib>Shi, Bin</creatorcontrib><creatorcontrib>He, Lin</creatorcontrib><creatorcontrib>Shi, Jun-Wei</creatorcontrib><creatorcontrib>Xiao, Wen-Jing</creatorcontrib><creatorcontrib>Lu, Liang-Qiu</creatorcontrib><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Materials Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Organic Chemistry Frontiers</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Qu, Bao-Le</au><au>Shi, Bin</au><au>He, Lin</au><au>Shi, Jun-Wei</au><au>Xiao, Wen-Jing</au><au>Lu, Liang-Qiu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Photoinduced carbene transfer for copper-catalyzed asymmetric [4 + 1] cycloadditions: an entry to chiral indolines bearing quaternary stereocenters</atitle><jtitle>Organic Chemistry Frontiers</jtitle><date>2023-07-11</date><risdate>2023</risdate><volume>10</volume><issue>14</issue><spage>3498</spage><epage>3503</epage><pages>3498-3503</pages><issn>2052-4129</issn><issn>2052-4110</issn><eissn>2052-4129</eissn><eissn>2052-4110</eissn><abstract>Indoline skeletons are widely found in many natural isolates and pharmaceuticals, making indoline synthesis an ongoing research hotspot in synthetic chemistry. However, the catalytic asymmetric
de novo
construction of indolines bearing chiral quaternary stereocenters remains challenging. Herein, we present a solution to this unmet challenge through copper-catalyzed asymmetric [4 + 1] cycloadditions of ethynylbenzoxazinones with sulfur ylides, which are formed
in situ
by photoinduced carbene transfer. As a result, a wide range of chiral indolines bearing C2-quaternary stereocenters are obtained with good enantio- and diastereoselectivities (up to 19 : 1 dr and 96 : 4 er).</abstract><cop>London</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/D3QO00551H</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-9318-6021</orcidid><orcidid>https://orcid.org/0000-0003-2177-4729</orcidid></addata></record> |
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| identifier | ISSN: 2052-4129 |
| ispartof | Organic Chemistry Frontiers, 2023-07, Vol.10 (14), p.3498-3503 |
| issn | 2052-4129 2052-4110 2052-4129 2052-4110 |
| language | eng |
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| source | Royal Society Of Chemistry Journals 2008- |
| subjects | Asymmetry Carbenes Copper Heterocyclic compounds Organic chemistry Sulfur |
| title | Photoinduced carbene transfer for copper-catalyzed asymmetric [4 + 1] cycloadditions: an entry to chiral indolines bearing quaternary stereocenters |
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