Catalytic Regio‐ and Enantioselective [4+2] Annulation Reactions of Non‐activated Allenes by a Chiral Cationic Indium Complex
Regio‐ and enantioselective [4+2] annulation between β,γ‐unsaturated α‐keto esters and non‐activated allenes was achieved by using a chiral cationic indium(III)/phosphate catalyst. The reaction affords the corresponding C3‐selective dihydropyrans in good yields and with high enantioselectivity (up t...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2017-08, Vol.56 (36), p.10867-10871 |
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| container_issue | 36 |
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| container_title | Angewandte Chemie International Edition |
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| creator | Wang, Le Lv, Jian Zhang, Long Luo, Sanzhong |
| description | Regio‐ and enantioselective [4+2] annulation between β,γ‐unsaturated α‐keto esters and non‐activated allenes was achieved by using a chiral cationic indium(III)/phosphate catalyst. The reaction affords the corresponding C3‐selective dihydropyrans in good yields and with high enantioselectivity (up to 99 % ee).
Full circle: A chiral cationic indium phosphate complex was identified that enables unprecedented [4+2] annulation between β,γ‐unsaturated α‐keto esters and non‐activated allenes. The reaction affords C3‐selective adducts in good yields and with high enantioselectivity. |
| doi_str_mv | 10.1002/anie.201704020 |
| format | Article |
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Full circle: A chiral cationic indium phosphate complex was identified that enables unprecedented [4+2] annulation between β,γ‐unsaturated α‐keto esters and non‐activated allenes. The reaction affords C3‐selective adducts in good yields and with high enantioselectivity.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201704020</identifier><identifier>PMID: 28707819</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>[4+2] annulation ; allenes ; Catalysts ; Cations ; Chemical reactions ; chiral phosphates ; Enantiomers ; Esters ; homogeneous catalysis ; Indium ; Indium phosphates ; Organic chemistry ; Phosphates</subject><ispartof>Angewandte Chemie International Edition, 2017-08, Vol.56 (36), p.10867-10871</ispartof><rights>2017 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4760-caeaf604ab9e19caff9382f3b18dfc4a2f599ca79d27a1a1cc283ae16c8af8773</citedby><cites>FETCH-LOGICAL-c4760-caeaf604ab9e19caff9382f3b18dfc4a2f599ca79d27a1a1cc283ae16c8af8773</cites><orcidid>0000-0001-8714-4047</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.201704020$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201704020$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27903,27904,45553,45554</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28707819$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wang, Le</creatorcontrib><creatorcontrib>Lv, Jian</creatorcontrib><creatorcontrib>Zhang, Long</creatorcontrib><creatorcontrib>Luo, Sanzhong</creatorcontrib><title>Catalytic Regio‐ and Enantioselective [4+2] Annulation Reactions of Non‐activated Allenes by a Chiral Cationic Indium Complex</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>Regio‐ and enantioselective [4+2] annulation between β,γ‐unsaturated α‐keto esters and non‐activated allenes was achieved by using a chiral cationic indium(III)/phosphate catalyst. The reaction affords the corresponding C3‐selective dihydropyrans in good yields and with high enantioselectivity (up to 99 % ee).
Full circle: A chiral cationic indium phosphate complex was identified that enables unprecedented [4+2] annulation between β,γ‐unsaturated α‐keto esters and non‐activated allenes. The reaction affords C3‐selective adducts in good yields and with high enantioselectivity.</description><subject>[4+2] annulation</subject><subject>allenes</subject><subject>Catalysts</subject><subject>Cations</subject><subject>Chemical reactions</subject><subject>chiral phosphates</subject><subject>Enantiomers</subject><subject>Esters</subject><subject>homogeneous catalysis</subject><subject>Indium</subject><subject>Indium phosphates</subject><subject>Organic chemistry</subject><subject>Phosphates</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqFkc-KFDEQxoMo7rp69SgBLwvSY_70TJLj0Iw6sKwgehJpatIVzZJOxk736tz0DXxGn8S0s67gxVMVVb_vS6iPkMecLThj4jlEjwvBuGI1E-wOOeVLwSuplLxb-lrKSuklPyEPcr4qvNZsdZ-cCK2Y0tycku8NjBAOo7f0DX706ee3HxRiRzcR4uhTxoB29NdI39fPxAe6jnEKUBax4GDnJtPk6GWKRTkPrmHEjq5DwIiZ7g4UaPPJDxBo81tXHtrGzk89bVK_D_j1IbnnIGR8dFPPyLsXm7fNq-ri9ctts76obK1WrLKA4Fashp1Bbiw4Z6QWTu647pytQbilKWNlOqGAA7dWaAnIV1aD0-UeZ-T86Lsf0ucJ89j2PlsMASKmKbfciHJBKeoZffoPepWmIZbfFUpyUWumTKEWR8oOKecBXbsffA_DoeWsncNp53Da23CK4MmN7bTrsbvF_6RRAHMEvviAh__YtevL7eav-S9coJ4c</recordid><startdate>20170828</startdate><enddate>20170828</enddate><creator>Wang, Le</creator><creator>Lv, Jian</creator><creator>Zhang, Long</creator><creator>Luo, Sanzhong</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/0000-0001-8714-4047</orcidid></search><sort><creationdate>20170828</creationdate><title>Catalytic Regio‐ and Enantioselective [4+2] Annulation Reactions of Non‐activated Allenes by a Chiral Cationic Indium Complex</title><author>Wang, Le ; Lv, Jian ; Zhang, Long ; Luo, Sanzhong</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4760-caeaf604ab9e19caff9382f3b18dfc4a2f599ca79d27a1a1cc283ae16c8af8773</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>[4+2] annulation</topic><topic>allenes</topic><topic>Catalysts</topic><topic>Cations</topic><topic>Chemical reactions</topic><topic>chiral phosphates</topic><topic>Enantiomers</topic><topic>Esters</topic><topic>homogeneous catalysis</topic><topic>Indium</topic><topic>Indium phosphates</topic><topic>Organic chemistry</topic><topic>Phosphates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wang, Le</creatorcontrib><creatorcontrib>Lv, Jian</creatorcontrib><creatorcontrib>Zhang, Long</creatorcontrib><creatorcontrib>Luo, Sanzhong</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>Wang, Le</au><au>Lv, Jian</au><au>Zhang, Long</au><au>Luo, Sanzhong</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Catalytic Regio‐ and Enantioselective [4+2] Annulation Reactions of Non‐activated Allenes by a Chiral Cationic Indium Complex</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2017-08-28</date><risdate>2017</risdate><volume>56</volume><issue>36</issue><spage>10867</spage><epage>10871</epage><pages>10867-10871</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>Regio‐ and enantioselective [4+2] annulation between β,γ‐unsaturated α‐keto esters and non‐activated allenes was achieved by using a chiral cationic indium(III)/phosphate catalyst. The reaction affords the corresponding C3‐selective dihydropyrans in good yields and with high enantioselectivity (up to 99 % ee).
Full circle: A chiral cationic indium phosphate complex was identified that enables unprecedented [4+2] annulation between β,γ‐unsaturated α‐keto esters and non‐activated allenes. The reaction affords C3‐selective adducts in good yields and with high enantioselectivity.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>28707819</pmid><doi>10.1002/anie.201704020</doi><tpages>5</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0001-8714-4047</orcidid></addata></record> |
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| identifier | ISSN: 1433-7851 |
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| language | eng |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | [4+2] annulation allenes Catalysts Cations Chemical reactions chiral phosphates Enantiomers Esters homogeneous catalysis Indium Indium phosphates Organic chemistry Phosphates |
| title | Catalytic Regio‐ and Enantioselective [4+2] Annulation Reactions of Non‐activated Allenes by a Chiral Cationic Indium Complex |
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