Dearomative tandem annulation to access chiral indoline-fused bicyclo[2.2.2]octanes using modularly designed organocatalysts
Herein, we describe an asymmetric dearomative tandem annulation between 3-nitroindoles and 7-oxo-5-heptenals. The cascade reactions proceeded smoothly using modularly designed organocatalysts self-assembled from cinchona-squaramide and d -proline. As a result, a collection of enantioenriched indolin...
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| Veröffentlicht in: | Organic Chemistry Frontiers 2023-02, Vol.10 (5), p.1237-1244 |
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| container_title | Organic Chemistry Frontiers |
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| creator | Zou, Wen-Lin Liu, Yan-Qing Li, Qing-Zhu Kou, Xin-Xin Huang, Hua Tong, Rong-Sheng Li, Jun-Long Han, Bo |
| description | Herein, we describe an asymmetric dearomative tandem annulation between 3-nitroindoles and 7-oxo-5-heptenals. The cascade reactions proceeded smoothly using modularly designed organocatalysts self-assembled from cinchona-squaramide and
d
-proline. As a result, a collection of enantioenriched indoline-fused bicyclo[2.2.2]octanes featuring six vicinal stereocenters were smoothly obtained in good yields with excellent enantioselectivities (up to >99% ee). This protocol provides an economical and practical approach for the asymmetric synthesis of structurally complex indolines. |
| doi_str_mv | 10.1039/D2QO01859D |
| format | Article |
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d
-proline. As a result, a collection of enantioenriched indoline-fused bicyclo[2.2.2]octanes featuring six vicinal stereocenters were smoothly obtained in good yields with excellent enantioselectivities (up to >99% ee). This protocol provides an economical and practical approach for the asymmetric synthesis of structurally complex indolines.</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/D2QO01859D</identifier><language>eng</language><publisher>London: Royal Society of Chemistry</publisher><subject>Asymmetric synthesis ; Asymmetry ; Cascade chemical reactions ; Chemical reactions ; Heterocyclic compounds ; Modular design ; Octanes ; Organic chemistry ; Self-assembly</subject><ispartof>Organic Chemistry Frontiers, 2023-02, Vol.10 (5), p.1237-1244</ispartof><rights>Copyright Royal Society of Chemistry 2023</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c281t-2417b5e5c254bf612ba2fc4e86b7a47b5f1bbc56c9560bc9eda51c77f0f227313</citedby><cites>FETCH-LOGICAL-c281t-2417b5e5c254bf612ba2fc4e86b7a47b5f1bbc56c9560bc9eda51c77f0f227313</cites><orcidid>0000-0003-3200-4682 ; 0000-0002-4700-0142</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Zou, Wen-Lin</creatorcontrib><creatorcontrib>Liu, Yan-Qing</creatorcontrib><creatorcontrib>Li, Qing-Zhu</creatorcontrib><creatorcontrib>Kou, Xin-Xin</creatorcontrib><creatorcontrib>Huang, Hua</creatorcontrib><creatorcontrib>Tong, Rong-Sheng</creatorcontrib><creatorcontrib>Li, Jun-Long</creatorcontrib><creatorcontrib>Han, Bo</creatorcontrib><title>Dearomative tandem annulation to access chiral indoline-fused bicyclo[2.2.2]octanes using modularly designed organocatalysts</title><title>Organic Chemistry Frontiers</title><description>Herein, we describe an asymmetric dearomative tandem annulation between 3-nitroindoles and 7-oxo-5-heptenals. The cascade reactions proceeded smoothly using modularly designed organocatalysts self-assembled from cinchona-squaramide and
d
-proline. As a result, a collection of enantioenriched indoline-fused bicyclo[2.2.2]octanes featuring six vicinal stereocenters were smoothly obtained in good yields with excellent enantioselectivities (up to >99% ee). This protocol provides an economical and practical approach for the asymmetric synthesis of structurally complex indolines.</description><subject>Asymmetric synthesis</subject><subject>Asymmetry</subject><subject>Cascade chemical reactions</subject><subject>Chemical reactions</subject><subject>Heterocyclic compounds</subject><subject>Modular design</subject><subject>Octanes</subject><subject>Organic chemistry</subject><subject>Self-assembly</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>eNpNkE9LxDAQxYMouKx78RMEvAldk2nTtEfZ9R8Ii6AnkZKkyZqlTdakFQp-eCMrKHOYYebHe8xD6JySJSV5fbWGpw2hFavXR2gGhEFWUKiP_82naBHjjhBCgZWE8Rn6WmsRfC8G-6nxIFyreyycG7u08Q4PHguldIxYvdsgOmxd6zvrdGbGqFssrZpU519hmerNq6SgIx6jdVvc-zbJhG7CrY526xLuw1Y4r8QguikO8QydGNFFvfjtc_Rye_O8us8eN3cPq-vHTEFFhwwKyiXTTAErpCkpSAFGFboqJRdFOhkqpWKlqtNTUtW6FYwqzg0xADyn-RxdHHT3wX-MOg7Nzo_BJcsGeEXyqipqSNTlgVLBxxi0afbB9iJMDSXNT8DNX8D5NwUZb7Y</recordid><startdate>20230228</startdate><enddate>20230228</enddate><creator>Zou, Wen-Lin</creator><creator>Liu, Yan-Qing</creator><creator>Li, Qing-Zhu</creator><creator>Kou, Xin-Xin</creator><creator>Huang, Hua</creator><creator>Tong, Rong-Sheng</creator><creator>Li, Jun-Long</creator><creator>Han, Bo</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/0000-0003-3200-4682</orcidid><orcidid>https://orcid.org/0000-0002-4700-0142</orcidid></search><sort><creationdate>20230228</creationdate><title>Dearomative tandem annulation to access chiral indoline-fused bicyclo[2.2.2]octanes using modularly designed organocatalysts</title><author>Zou, Wen-Lin ; Liu, Yan-Qing ; Li, Qing-Zhu ; Kou, Xin-Xin ; Huang, Hua ; Tong, Rong-Sheng ; Li, Jun-Long ; Han, Bo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c281t-2417b5e5c254bf612ba2fc4e86b7a47b5f1bbc56c9560bc9eda51c77f0f227313</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Asymmetric synthesis</topic><topic>Asymmetry</topic><topic>Cascade chemical reactions</topic><topic>Chemical reactions</topic><topic>Heterocyclic compounds</topic><topic>Modular design</topic><topic>Octanes</topic><topic>Organic chemistry</topic><topic>Self-assembly</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zou, Wen-Lin</creatorcontrib><creatorcontrib>Liu, Yan-Qing</creatorcontrib><creatorcontrib>Li, Qing-Zhu</creatorcontrib><creatorcontrib>Kou, Xin-Xin</creatorcontrib><creatorcontrib>Huang, Hua</creatorcontrib><creatorcontrib>Tong, Rong-Sheng</creatorcontrib><creatorcontrib>Li, Jun-Long</creatorcontrib><creatorcontrib>Han, Bo</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>Zou, Wen-Lin</au><au>Liu, Yan-Qing</au><au>Li, Qing-Zhu</au><au>Kou, Xin-Xin</au><au>Huang, Hua</au><au>Tong, Rong-Sheng</au><au>Li, Jun-Long</au><au>Han, Bo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Dearomative tandem annulation to access chiral indoline-fused bicyclo[2.2.2]octanes using modularly designed organocatalysts</atitle><jtitle>Organic Chemistry Frontiers</jtitle><date>2023-02-28</date><risdate>2023</risdate><volume>10</volume><issue>5</issue><spage>1237</spage><epage>1244</epage><pages>1237-1244</pages><issn>2052-4129</issn><issn>2052-4110</issn><eissn>2052-4129</eissn><eissn>2052-4110</eissn><abstract>Herein, we describe an asymmetric dearomative tandem annulation between 3-nitroindoles and 7-oxo-5-heptenals. The cascade reactions proceeded smoothly using modularly designed organocatalysts self-assembled from cinchona-squaramide and
d
-proline. As a result, a collection of enantioenriched indoline-fused bicyclo[2.2.2]octanes featuring six vicinal stereocenters were smoothly obtained in good yields with excellent enantioselectivities (up to >99% ee). This protocol provides an economical and practical approach for the asymmetric synthesis of structurally complex indolines.</abstract><cop>London</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/D2QO01859D</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0003-3200-4682</orcidid><orcidid>https://orcid.org/0000-0002-4700-0142</orcidid></addata></record> |
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| identifier | ISSN: 2052-4129 |
| ispartof | Organic Chemistry Frontiers, 2023-02, Vol.10 (5), p.1237-1244 |
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| language | eng |
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| source | Royal Society Of Chemistry Journals 2008- |
| subjects | Asymmetric synthesis Asymmetry Cascade chemical reactions Chemical reactions Heterocyclic compounds Modular design Octanes Organic chemistry Self-assembly |
| title | Dearomative tandem annulation to access chiral indoline-fused bicyclo[2.2.2]octanes using modularly designed organocatalysts |
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