Enantioselective Dearomatization of Indoles by an Azoalkene‐Enabled (3+2) Reaction: Access to Pyrroloindolines
The enantioselective dearomatization of indoles by an organocatalytic (3+2) reaction has been established. The reaction makes use of simple indole derivatives as substrates, and employs azoalkenes reaction partners. A wide range of pyrroloindolines containing an all‐carbon quaternary stereogenic cen...
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| Veröffentlicht in: | Angewandte Chemie 2020-01, Vol.132 (2), p.658-662 |
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| container_title | Angewandte Chemie |
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| creator | Mei, Guang‐Jian Tang, Xiwen Tasdan, Yildiz Lu, Yixin |
| description | The enantioselective dearomatization of indoles by an organocatalytic (3+2) reaction has been established. The reaction makes use of simple indole derivatives as substrates, and employs azoalkenes reaction partners. A wide range of pyrroloindolines containing an all‐carbon quaternary stereogenic center were readily prepared in high yields and with excellent enantioselectivities.
Ganz einfach: Eine enantioselektive Dearomatisierung von Indolen durch eine organokatalytische (3+2)‐Reaktion nutzt einfache Indolderivate als Substrate und Azoalkene als 1,3‐Dipol‐Reaktionspartner. Ein breites Spektrum an Pyrroloindolinen mit einem quartären All‐Kohlenstoff‐Stereozentrum wurde leicht in hohen Ausbeuten und mit exzellenten Enantioselektivitäten hergestellt. |
| doi_str_mv | 10.1002/ange.201911686 |
| format | Article |
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Ganz einfach: Eine enantioselektive Dearomatisierung von Indolen durch eine organokatalytische (3+2)‐Reaktion nutzt einfache Indolderivate als Substrate und Azoalkene als 1,3‐Dipol‐Reaktionspartner. Ein breites Spektrum an Pyrroloindolinen mit einem quartären All‐Kohlenstoff‐Stereozentrum wurde leicht in hohen Ausbeuten und mit exzellenten Enantioselektivitäten hergestellt.</description><identifier>ISSN: 0044-8249</identifier><identifier>EISSN: 1521-3757</identifier><identifier>DOI: 10.1002/ange.201911686</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Chemistry ; Dearomatisierung ; Enantiomers ; Enantioselektivität ; Heterocyclen ; Indoles ; Organokatalyse ; Substrates ; Synthesemethoden</subject><ispartof>Angewandte Chemie, 2020-01, Vol.132 (2), p.658-662</ispartof><rights>2020 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c1626-fc73cf88a3673c5a668d25ef12158016c584e8c567e924dfa02fb49164ec10973</citedby><cites>FETCH-LOGICAL-c1626-fc73cf88a3673c5a668d25ef12158016c584e8c567e924dfa02fb49164ec10973</cites><orcidid>0000-0002-5730-166X</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%2Fange.201911686$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fange.201911686$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Mei, Guang‐Jian</creatorcontrib><creatorcontrib>Tang, Xiwen</creatorcontrib><creatorcontrib>Tasdan, Yildiz</creatorcontrib><creatorcontrib>Lu, Yixin</creatorcontrib><title>Enantioselective Dearomatization of Indoles by an Azoalkene‐Enabled (3+2) Reaction: Access to Pyrroloindolines</title><title>Angewandte Chemie</title><description>The enantioselective dearomatization of indoles by an organocatalytic (3+2) reaction has been established. The reaction makes use of simple indole derivatives as substrates, and employs azoalkenes reaction partners. A wide range of pyrroloindolines containing an all‐carbon quaternary stereogenic center were readily prepared in high yields and with excellent enantioselectivities.
Ganz einfach: Eine enantioselektive Dearomatisierung von Indolen durch eine organokatalytische (3+2)‐Reaktion nutzt einfache Indolderivate als Substrate und Azoalkene als 1,3‐Dipol‐Reaktionspartner. Ein breites Spektrum an Pyrroloindolinen mit einem quartären All‐Kohlenstoff‐Stereozentrum wurde leicht in hohen Ausbeuten und mit exzellenten Enantioselektivitäten hergestellt.</description><subject>Chemistry</subject><subject>Dearomatisierung</subject><subject>Enantiomers</subject><subject>Enantioselektivität</subject><subject>Heterocyclen</subject><subject>Indoles</subject><subject>Organokatalyse</subject><subject>Substrates</subject><subject>Synthesemethoden</subject><issn>0044-8249</issn><issn>1521-3757</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNqFkEFLwzAUx4MoOKdXzwEvinQmaZum3sacczBURM8hS1-ks0tm0indyY_gZ_ST2DLRo4fHe4ff7__gj9AxJQNKCLtQ9hkGjNCcUi74DurRlNEoztJsF_UISZJIsCTfRwchLAghnGV5D63GVtm6dAEq0HX5BvgKlHdLVZebdpzFzuCpLVwFAc8brCwebpyqXsDC18dna88rKPBpfM7O8AMo3TmXeKg1hIBrh-8b713lyi6itBAO0Z5RVYCjn91HT9fjx9FNNLubTEfDWaQpZzwyOou1EULFvD1SxbkoWAqGMpoKQrlORQJCpzyDnCWFUYSZeZJTnoCmJM_iPjrZ5q68e11DqOXCrb1tX0oWxzTrcmhLDbaU9i4ED0aufLlUvpGUyK5V2bUqf1tthXwrvJcVNP_Qcng7Gf-53yDAfHM</recordid><startdate>20200107</startdate><enddate>20200107</enddate><creator>Mei, Guang‐Jian</creator><creator>Tang, Xiwen</creator><creator>Tasdan, Yildiz</creator><creator>Lu, Yixin</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0002-5730-166X</orcidid></search><sort><creationdate>20200107</creationdate><title>Enantioselective Dearomatization of Indoles by an Azoalkene‐Enabled (3+2) Reaction: Access to Pyrroloindolines</title><author>Mei, Guang‐Jian ; Tang, Xiwen ; Tasdan, Yildiz ; Lu, Yixin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c1626-fc73cf88a3673c5a668d25ef12158016c584e8c567e924dfa02fb49164ec10973</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Chemistry</topic><topic>Dearomatisierung</topic><topic>Enantiomers</topic><topic>Enantioselektivität</topic><topic>Heterocyclen</topic><topic>Indoles</topic><topic>Organokatalyse</topic><topic>Substrates</topic><topic>Synthesemethoden</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mei, Guang‐Jian</creatorcontrib><creatorcontrib>Tang, Xiwen</creatorcontrib><creatorcontrib>Tasdan, Yildiz</creatorcontrib><creatorcontrib>Lu, Yixin</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Angewandte Chemie</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Mei, Guang‐Jian</au><au>Tang, Xiwen</au><au>Tasdan, Yildiz</au><au>Lu, Yixin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enantioselective Dearomatization of Indoles by an Azoalkene‐Enabled (3+2) Reaction: Access to Pyrroloindolines</atitle><jtitle>Angewandte Chemie</jtitle><date>2020-01-07</date><risdate>2020</risdate><volume>132</volume><issue>2</issue><spage>658</spage><epage>662</epage><pages>658-662</pages><issn>0044-8249</issn><eissn>1521-3757</eissn><abstract>The enantioselective dearomatization of indoles by an organocatalytic (3+2) reaction has been established. The reaction makes use of simple indole derivatives as substrates, and employs azoalkenes reaction partners. A wide range of pyrroloindolines containing an all‐carbon quaternary stereogenic center were readily prepared in high yields and with excellent enantioselectivities.
Ganz einfach: Eine enantioselektive Dearomatisierung von Indolen durch eine organokatalytische (3+2)‐Reaktion nutzt einfache Indolderivate als Substrate und Azoalkene als 1,3‐Dipol‐Reaktionspartner. Ein breites Spektrum an Pyrroloindolinen mit einem quartären All‐Kohlenstoff‐Stereozentrum wurde leicht in hohen Ausbeuten und mit exzellenten Enantioselektivitäten hergestellt.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ange.201911686</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-5730-166X</orcidid></addata></record> |
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| subjects | Chemistry Dearomatisierung Enantiomers Enantioselektivität Heterocyclen Indoles Organokatalyse Substrates Synthesemethoden |
| title | Enantioselective Dearomatization of Indoles by an Azoalkene‐Enabled (3+2) Reaction: Access to Pyrroloindolines |
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