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Stereoselective Synthesis of Polycycles Containing an Aziridine Group: Intramolecular aza-Diels-Alder Reactions of Unactivated 2H-Azirines with Unactivated Dienes
Vinyl azide with a pendent diene can undergo thermal decomposition to a related azirine intermediate, which was used immediately in an intramolecular aza‐Diels–Alder reaction to furnish an aziridine‐containing trans‐fused tricyclic core structure with excellent stereoselectivity. The method provides...
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| Published in: | Angewandte Chemie 2016-02, Vol.128 (7), p.2586-2590 |
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| Main Authors: | , , , , , , , |
| Format: | Article |
| Language: | eng ; ger |
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| container_end_page | 2590 |
| container_issue | 7 |
| container_start_page | 2586 |
| container_title | Angewandte Chemie |
| container_volume | 128 |
| creator | Xu, Hua-Dong Zhou, Hao Pan, Ying-Peng Ren, Xin-Tao Wu, Hao Han, Mei Han, Run-Ze Shen, Mei-Hua |
| description | Vinyl azide with a pendent diene can undergo thermal decomposition to a related azirine intermediate, which was used immediately in an intramolecular aza‐Diels–Alder reaction to furnish an aziridine‐containing trans‐fused tricyclic core structure with excellent stereoselectivity. The method provides a facile entry to complex polycyclic alkaliods which can be further elaborated by ring‐opening reactions and ring expansion of the aziridine moiety, as well as by dihydroxylation of the alkene group.
Sichere Variante: 5‐6‐3‐ und 6‐6‐3‐Tricyclen sowie komplexere Polycyclen mit konjugiertem Aziridinring wurden durch eine intramolekulare Aza‐Diels‐Alder‐Reaktion von 2H‐Azirin hoch stereoselektiv aufgebaut. Die In‐situ‐Bildung der Azirine aus Vinylazid‐Vorstufen vermeidet Probleme durch ihre direkte Handhabung. |
| doi_str_mv | 10.1002/ange.201510096 |
| format | article |
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Sichere Variante: 5‐6‐3‐ und 6‐6‐3‐Tricyclen sowie komplexere Polycyclen mit konjugiertem Aziridinring wurden durch eine intramolekulare Aza‐Diels‐Alder‐Reaktion von 2H‐Azirin hoch stereoselektiv aufgebaut. Die In‐situ‐Bildung der Azirine aus Vinylazid‐Vorstufen vermeidet Probleme durch ihre direkte Handhabung.</description><identifier>ISSN: 0044-8249</identifier><identifier>EISSN: 1521-3757</identifier><identifier>DOI: 10.1002/ange.201510096</identifier><language>eng ; ger</language><publisher>Weinheim: Blackwell Publishing Ltd</publisher><subject>Alkenes ; Aziridine ; Chemical synthesis ; Chemistry ; Cycloadditionen ; Diels-Alder reactions ; Dienes ; Heterocyclen ; Kleinringsysteme ; Olefins ; Rings (mathematics) ; Stereoselectivity ; Synthesemethoden ; Synthesis (chemistry) ; Thermal decomposition</subject><ispartof>Angewandte Chemie, 2016-02, Vol.128 (7), p.2586-2590</ispartof><rights>2016 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c2166-95da8b302b43f26a2efe7d2628f16bb97493a47fec6ef33e882af934df3e166f3</cites></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>Xu, Hua-Dong</creatorcontrib><creatorcontrib>Zhou, Hao</creatorcontrib><creatorcontrib>Pan, Ying-Peng</creatorcontrib><creatorcontrib>Ren, Xin-Tao</creatorcontrib><creatorcontrib>Wu, Hao</creatorcontrib><creatorcontrib>Han, Mei</creatorcontrib><creatorcontrib>Han, Run-Ze</creatorcontrib><creatorcontrib>Shen, Mei-Hua</creatorcontrib><title>Stereoselective Synthesis of Polycycles Containing an Aziridine Group: Intramolecular aza-Diels-Alder Reactions of Unactivated 2H-Azirines with Unactivated Dienes</title><title>Angewandte Chemie</title><addtitle>Angew. Chem</addtitle><description>Vinyl azide with a pendent diene can undergo thermal decomposition to a related azirine intermediate, which was used immediately in an intramolecular aza‐Diels–Alder reaction to furnish an aziridine‐containing trans‐fused tricyclic core structure with excellent stereoselectivity. The method provides a facile entry to complex polycyclic alkaliods which can be further elaborated by ring‐opening reactions and ring expansion of the aziridine moiety, as well as by dihydroxylation of the alkene group.
Sichere Variante: 5‐6‐3‐ und 6‐6‐3‐Tricyclen sowie komplexere Polycyclen mit konjugiertem Aziridinring wurden durch eine intramolekulare Aza‐Diels‐Alder‐Reaktion von 2H‐Azirin hoch stereoselektiv aufgebaut. Die In‐situ‐Bildung der Azirine aus Vinylazid‐Vorstufen vermeidet Probleme durch ihre direkte Handhabung.</description><subject>Alkenes</subject><subject>Aziridine</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Cycloadditionen</subject><subject>Diels-Alder reactions</subject><subject>Dienes</subject><subject>Heterocyclen</subject><subject>Kleinringsysteme</subject><subject>Olefins</subject><subject>Rings (mathematics)</subject><subject>Stereoselectivity</subject><subject>Synthesemethoden</subject><subject>Synthesis (chemistry)</subject><subject>Thermal decomposition</subject><issn>0044-8249</issn><issn>1521-3757</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNqFks1uEzEURkcIJEJhy9oSGzYT_BePzS5KS1KpKqilsLScmevWxbFTe6Zl-jg8KU6DKmABK-va53zX8nVVvSZ4SjCm70y4hCnFZFYqJZ5UEzKjpGbNrHlaTTDmvJaUq-fVi5yvMcaCNmpS_TjvIUHM4KHt3S2g8zH0V5BdRtGiT9GP7dh6yGgRQ29ccOESmYDm9y65zgVAyxSH7Xt0HPpkNrGkDN4kZO5NfejA53ruO0joDEyJj-Eh9SLsilvTQ4foqn7ICqXFneuv_jgsCWX_ZfXMGp_h1a_1oLr4cPR5sapPPi6PF_OTuqVEiFrNOiPXDNM1Z5YKQ8FC01FBpSVivVYNV8zwxkIrwDIGUlJjFeOdZVB8yw6qt_vcbYo3A-Reb1xuwXsTIA5ZE1keUWJOWEHf_IVexyGFcjtNFBZEUc7xP6lGUMIbpWShpnuqTTHnBFZvk9uYNGqC9W6wejdY_TjYIqi9cOc8jP-h9fx0efS7W-9dl3v4_uia9E2LpnwV_fV0qaU4k4cr9UVz9hNOhrhA</recordid><startdate>20160212</startdate><enddate>20160212</enddate><creator>Xu, Hua-Dong</creator><creator>Zhou, Hao</creator><creator>Pan, Ying-Peng</creator><creator>Ren, Xin-Tao</creator><creator>Wu, Hao</creator><creator>Han, Mei</creator><creator>Han, Run-Ze</creator><creator>Shen, Mei-Hua</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20160212</creationdate><title>Stereoselective Synthesis of Polycycles Containing an Aziridine Group: Intramolecular aza-Diels-Alder Reactions of Unactivated 2H-Azirines with Unactivated Dienes</title><author>Xu, Hua-Dong ; Zhou, Hao ; Pan, Ying-Peng ; Ren, Xin-Tao ; Wu, Hao ; Han, Mei ; Han, Run-Ze ; Shen, Mei-Hua</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2166-95da8b302b43f26a2efe7d2628f16bb97493a47fec6ef33e882af934df3e166f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng ; ger</language><creationdate>2016</creationdate><topic>Alkenes</topic><topic>Aziridine</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Cycloadditionen</topic><topic>Diels-Alder reactions</topic><topic>Dienes</topic><topic>Heterocyclen</topic><topic>Kleinringsysteme</topic><topic>Olefins</topic><topic>Rings (mathematics)</topic><topic>Stereoselectivity</topic><topic>Synthesemethoden</topic><topic>Synthesis (chemistry)</topic><topic>Thermal decomposition</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Xu, Hua-Dong</creatorcontrib><creatorcontrib>Zhou, Hao</creatorcontrib><creatorcontrib>Pan, Ying-Peng</creatorcontrib><creatorcontrib>Ren, Xin-Tao</creatorcontrib><creatorcontrib>Wu, Hao</creatorcontrib><creatorcontrib>Han, Mei</creatorcontrib><creatorcontrib>Han, Run-Ze</creatorcontrib><creatorcontrib>Shen, Mei-Hua</creatorcontrib><collection>Istex</collection><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>Xu, Hua-Dong</au><au>Zhou, Hao</au><au>Pan, Ying-Peng</au><au>Ren, Xin-Tao</au><au>Wu, Hao</au><au>Han, Mei</au><au>Han, Run-Ze</au><au>Shen, Mei-Hua</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Stereoselective Synthesis of Polycycles Containing an Aziridine Group: Intramolecular aza-Diels-Alder Reactions of Unactivated 2H-Azirines with Unactivated Dienes</atitle><jtitle>Angewandte Chemie</jtitle><addtitle>Angew. Chem</addtitle><date>2016-02-12</date><risdate>2016</risdate><volume>128</volume><issue>7</issue><spage>2586</spage><epage>2590</epage><pages>2586-2590</pages><issn>0044-8249</issn><eissn>1521-3757</eissn><abstract>Vinyl azide with a pendent diene can undergo thermal decomposition to a related azirine intermediate, which was used immediately in an intramolecular aza‐Diels–Alder reaction to furnish an aziridine‐containing trans‐fused tricyclic core structure with excellent stereoselectivity. The method provides a facile entry to complex polycyclic alkaliods which can be further elaborated by ring‐opening reactions and ring expansion of the aziridine moiety, as well as by dihydroxylation of the alkene group.
Sichere Variante: 5‐6‐3‐ und 6‐6‐3‐Tricyclen sowie komplexere Polycyclen mit konjugiertem Aziridinring wurden durch eine intramolekulare Aza‐Diels‐Alder‐Reaktion von 2H‐Azirin hoch stereoselektiv aufgebaut. Die In‐situ‐Bildung der Azirine aus Vinylazid‐Vorstufen vermeidet Probleme durch ihre direkte Handhabung.</abstract><cop>Weinheim</cop><pub>Blackwell Publishing Ltd</pub><doi>10.1002/ange.201510096</doi><tpages>5</tpages></addata></record> |
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| ispartof | Angewandte Chemie, 2016-02, Vol.128 (7), p.2586-2590 |
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| language | eng ; ger |
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| source | Wiley |
| subjects | Alkenes Aziridine Chemical synthesis Chemistry Cycloadditionen Diels-Alder reactions Dienes Heterocyclen Kleinringsysteme Olefins Rings (mathematics) Stereoselectivity Synthesemethoden Synthesis (chemistry) Thermal decomposition |
| title | Stereoselective Synthesis of Polycycles Containing an Aziridine Group: Intramolecular aza-Diels-Alder Reactions of Unactivated 2H-Azirines with Unactivated Dienes |
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