Catalytic Asymmetric Dearomatization of Indolyl Dihydropyridines through an Enamine Isomerization/Spirocyclization/Transfer Hydrogenation Sequence
A highly efficient synthesis of enantioenriched spiroindolines by catalytic asymmetric dearomatization of indolyl dihydropyridines through a chiral phosphoric acid catalyzed enamine isomerization/spirocyclization/transfer hydrogenation sequence has been developed. This reaction proceeds under mild r...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2018-03, Vol.57 (10), p.2653-2656 |
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| creator | Xia, Zi‐Lei Zheng, Chao Wang, Shou‐Guo You, Shu‐Li |
| description | A highly efficient synthesis of enantioenriched spiroindolines by catalytic asymmetric dearomatization of indolyl dihydropyridines through a chiral phosphoric acid catalyzed enamine isomerization/spirocyclization/transfer hydrogenation sequence has been developed. This reaction proceeds under mild reaction conditions, affording novel spiroindolines in good yields (up to 88 %) with excellent enantioselectivity (up to 97 % ee). DFT calculations provide insights into the reaction mechanism as well as the origin of stereochemistry.
Born to be mild: An efficient synthesis of enantioenriched spiroindolines by catalytic asymmetric dearomatization of indolyl dihydropyridines through a chiral phosphoric acid (CPA)‐catalyzed enamine isomerization/spirocyclization/transfer hydrogenation sequence was developed (HEH=Hantzsch ester). The reaction proceeds under mild reaction conditions to afford spiroindolines in good yields (up to 88 %) with excellent enantioselectivity (up to 97 % ee). |
| doi_str_mv | 10.1002/anie.201712435 |
| format | Article |
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Born to be mild: An efficient synthesis of enantioenriched spiroindolines by catalytic asymmetric dearomatization of indolyl dihydropyridines through a chiral phosphoric acid (CPA)‐catalyzed enamine isomerization/spirocyclization/transfer hydrogenation sequence was developed (HEH=Hantzsch ester). The reaction proceeds under mild reaction conditions to afford spiroindolines in good yields (up to 88 %) with excellent enantioselectivity (up to 97 % ee).</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201712435</identifier><identifier>PMID: 29327453</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>asymmetric catalysis ; Catalysis ; Chemical synthesis ; chiral phosphoric acid ; dearomatization ; Enantiomers ; Hydrogenation ; Isomerization ; Phosphoric acid ; Reaction mechanisms ; spiroindolines ; Stereochemistry ; transfer hydrogenation</subject><ispartof>Angewandte Chemie International Edition, 2018-03, Vol.57 (10), p.2653-2656</ispartof><rights>2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4765-63995c9caf6b312ed74f7edf856a35cef921b5a24b89ccbdcacc723c4fb4fb053</citedby><cites>FETCH-LOGICAL-c4765-63995c9caf6b312ed74f7edf856a35cef921b5a24b89ccbdcacc723c4fb4fb053</cites><orcidid>0000-0003-4586-8359</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%2Fanie.201712435$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201712435$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/29327453$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Xia, Zi‐Lei</creatorcontrib><creatorcontrib>Zheng, Chao</creatorcontrib><creatorcontrib>Wang, Shou‐Guo</creatorcontrib><creatorcontrib>You, Shu‐Li</creatorcontrib><title>Catalytic Asymmetric Dearomatization of Indolyl Dihydropyridines through an Enamine Isomerization/Spirocyclization/Transfer Hydrogenation Sequence</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>A highly efficient synthesis of enantioenriched spiroindolines by catalytic asymmetric dearomatization of indolyl dihydropyridines through a chiral phosphoric acid catalyzed enamine isomerization/spirocyclization/transfer hydrogenation sequence has been developed. This reaction proceeds under mild reaction conditions, affording novel spiroindolines in good yields (up to 88 %) with excellent enantioselectivity (up to 97 % ee). DFT calculations provide insights into the reaction mechanism as well as the origin of stereochemistry.
Born to be mild: An efficient synthesis of enantioenriched spiroindolines by catalytic asymmetric dearomatization of indolyl dihydropyridines through a chiral phosphoric acid (CPA)‐catalyzed enamine isomerization/spirocyclization/transfer hydrogenation sequence was developed (HEH=Hantzsch ester). The reaction proceeds under mild reaction conditions to afford spiroindolines in good yields (up to 88 %) with excellent enantioselectivity (up to 97 % ee).</description><subject>asymmetric catalysis</subject><subject>Catalysis</subject><subject>Chemical synthesis</subject><subject>chiral phosphoric acid</subject><subject>dearomatization</subject><subject>Enantiomers</subject><subject>Hydrogenation</subject><subject>Isomerization</subject><subject>Phosphoric acid</subject><subject>Reaction mechanisms</subject><subject>spiroindolines</subject><subject>Stereochemistry</subject><subject>transfer hydrogenation</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNqFkU1r3DAQhkVpadJtrz0WQy-5eKMPy7KOy2bbLITmkOQsZHmUVbClrWRT3J-RX1wtu0mhl4IGDcMz7wzzIvSZ4CXBmF5q72BJMRGEVoy_QeeEU1IyIdjbnFeMlaLh5Ax9SOkp802D6_fojEpGRcXZOXpe61H38-hMsUrzMMAYc3oFOoZBj-53juCLYIut70I_98WV281dDPs5us55SMW4i2F63BXaFxuvh1wrtikMEE_Nl3d7F4OZTf9SuI_aJwuxuD4oPYI_DrmDnxN4Ax_RO6v7BJ9O_wI9fNvcr6_Lm9vv2_XqpjSVqHlZMym5kUbbumWEQicqK6CzDa814waspKTlmlZtI41pO6ONEZSZyrb5Yc4W6OKou48hT06jGlwy0PfaQ5iSIrKRNcEiH3aBvv6DPoUp-rydohg3rJZMkEwtj5SJIaUIVu2jG3ScFcHq4JY6uKVe3coNX06yUztA94q_2JMBeQR-uR7m_8ip1Y_t5q_4HzJmpkU</recordid><startdate>20180301</startdate><enddate>20180301</enddate><creator>Xia, Zi‐Lei</creator><creator>Zheng, Chao</creator><creator>Wang, Shou‐Guo</creator><creator>You, Shu‐Li</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-4586-8359</orcidid></search><sort><creationdate>20180301</creationdate><title>Catalytic Asymmetric Dearomatization of Indolyl Dihydropyridines through an Enamine Isomerization/Spirocyclization/Transfer Hydrogenation Sequence</title><author>Xia, Zi‐Lei ; Zheng, Chao ; Wang, Shou‐Guo ; You, Shu‐Li</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4765-63995c9caf6b312ed74f7edf856a35cef921b5a24b89ccbdcacc723c4fb4fb053</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>asymmetric catalysis</topic><topic>Catalysis</topic><topic>Chemical synthesis</topic><topic>chiral phosphoric acid</topic><topic>dearomatization</topic><topic>Enantiomers</topic><topic>Hydrogenation</topic><topic>Isomerization</topic><topic>Phosphoric acid</topic><topic>Reaction mechanisms</topic><topic>spiroindolines</topic><topic>Stereochemistry</topic><topic>transfer hydrogenation</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Xia, Zi‐Lei</creatorcontrib><creatorcontrib>Zheng, Chao</creatorcontrib><creatorcontrib>Wang, Shou‐Guo</creatorcontrib><creatorcontrib>You, Shu‐Li</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Xia, Zi‐Lei</au><au>Zheng, Chao</au><au>Wang, Shou‐Guo</au><au>You, Shu‐Li</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Catalytic Asymmetric Dearomatization of Indolyl Dihydropyridines through an Enamine Isomerization/Spirocyclization/Transfer Hydrogenation Sequence</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2018-03-01</date><risdate>2018</risdate><volume>57</volume><issue>10</issue><spage>2653</spage><epage>2656</epage><pages>2653-2656</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>A highly efficient synthesis of enantioenriched spiroindolines by catalytic asymmetric dearomatization of indolyl dihydropyridines through a chiral phosphoric acid catalyzed enamine isomerization/spirocyclization/transfer hydrogenation sequence has been developed. This reaction proceeds under mild reaction conditions, affording novel spiroindolines in good yields (up to 88 %) with excellent enantioselectivity (up to 97 % ee). DFT calculations provide insights into the reaction mechanism as well as the origin of stereochemistry.
Born to be mild: An efficient synthesis of enantioenriched spiroindolines by catalytic asymmetric dearomatization of indolyl dihydropyridines through a chiral phosphoric acid (CPA)‐catalyzed enamine isomerization/spirocyclization/transfer hydrogenation sequence was developed (HEH=Hantzsch ester). The reaction proceeds under mild reaction conditions to afford spiroindolines in good yields (up to 88 %) with excellent enantioselectivity (up to 97 % ee).</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>29327453</pmid><doi>10.1002/anie.201712435</doi><tpages>4</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0003-4586-8359</orcidid></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | asymmetric catalysis Catalysis Chemical synthesis chiral phosphoric acid dearomatization Enantiomers Hydrogenation Isomerization Phosphoric acid Reaction mechanisms spiroindolines Stereochemistry transfer hydrogenation |
| title | Catalytic Asymmetric Dearomatization of Indolyl Dihydropyridines through an Enamine Isomerization/Spirocyclization/Transfer Hydrogenation Sequence |
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