Organocatalytic Enantioselective Nucleophilic Alkynylation of Allyl Fluorides Affording Chiral Skipped Ene-ynes
Asymmetric methods for preparation of chiral alkynyl‐containing compounds are in extremely high demand in many sectors of chemical research. In this work, we report the discovery of a general organocatalytic enantioselective alkynylation based on the idea of Si/F activation of the allylic C−F bond....
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| Veröffentlicht in: | Angewandte Chemie 2016-06, Vol.128 (23), p.6856-6860 |
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| container_issue | 23 |
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| container_title | Angewandte Chemie |
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| creator | Okusu, Satoshi Okazaki, Hiroki Tokunaga, Etsuko Soloshonok, Vadim A. Shibata, Norio |
| description | Asymmetric methods for preparation of chiral alkynyl‐containing compounds are in extremely high demand in many sectors of chemical research. In this work, we report the discovery of a general organocatalytic enantioselective alkynylation based on the idea of Si/F activation of the allylic C−F bond. This approach features reasonably broad substrate scope, functional group tolerance, and relatively neutral, mild, and operationally convenient reaction conditions; all of which bode well for the synthetic value of the discovered method. In particular, this method provides unique chiral skipped 1,4‐ene‐ynes having two kinds of versatile functional groups.
Nicht konjugiert, dafür chiral: Eine organokatalytische enantioselektive Alkinylierung verläuft unter Si/F‐Aktivierung der allylischen C‐F‐Bindung. Die Reaktion eignet sich für eine Reihe von Substraten, ist mit funktionellen Gruppen verträglich und ist unter milden, neutralen Bedingungen bequem auszuführen. |
| doi_str_mv | 10.1002/ange.201601928 |
| format | Article |
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Nicht konjugiert, dafür chiral: Eine organokatalytische enantioselektive Alkinylierung verläuft unter Si/F‐Aktivierung der allylischen C‐F‐Bindung. Die Reaktion eignet sich für eine Reihe von Substraten, ist mit funktionellen Gruppen verträglich und ist unter milden, neutralen Bedingungen bequem auszuführen.</description><identifier>ISSN: 0044-8249</identifier><identifier>EISSN: 1521-3757</identifier><identifier>DOI: 10.1002/ange.201601928</identifier><language>eng</language><publisher>Weinheim: Blackwell Publishing Ltd</publisher><subject>Activation ; Alkine ; Asymmetry ; Bonding ; Chemistry ; Demand ; Enantiomers ; Enantioselektive Synthesen ; Fluor ; Fluorides ; Functional groups ; Organokatalysatoren ; Silicium ; Silicon ; Tolerances ; YneS protein</subject><ispartof>Angewandte Chemie, 2016-06, Vol.128 (23), p.6856-6860</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><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3678-4187f31c3c7997a2b8470a2c2bf359366c095f8c188c7c1644b9b9dbd5fa9bef3</citedby><cites>FETCH-LOGICAL-c3678-4187f31c3c7997a2b8470a2c2bf359366c095f8c188c7c1644b9b9dbd5fa9bef3</cites></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.201601928$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fange.201601928$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,777,781,1413,27906,27907,45556,45557</link.rule.ids></links><search><creatorcontrib>Okusu, Satoshi</creatorcontrib><creatorcontrib>Okazaki, Hiroki</creatorcontrib><creatorcontrib>Tokunaga, Etsuko</creatorcontrib><creatorcontrib>Soloshonok, Vadim A.</creatorcontrib><creatorcontrib>Shibata, Norio</creatorcontrib><title>Organocatalytic Enantioselective Nucleophilic Alkynylation of Allyl Fluorides Affording Chiral Skipped Ene-ynes</title><title>Angewandte Chemie</title><addtitle>Angew. Chem</addtitle><description>Asymmetric methods for preparation of chiral alkynyl‐containing compounds are in extremely high demand in many sectors of chemical research. In this work, we report the discovery of a general organocatalytic enantioselective alkynylation based on the idea of Si/F activation of the allylic C−F bond. This approach features reasonably broad substrate scope, functional group tolerance, and relatively neutral, mild, and operationally convenient reaction conditions; all of which bode well for the synthetic value of the discovered method. In particular, this method provides unique chiral skipped 1,4‐ene‐ynes having two kinds of versatile functional groups.
Nicht konjugiert, dafür chiral: Eine organokatalytische enantioselektive Alkinylierung verläuft unter Si/F‐Aktivierung der allylischen C‐F‐Bindung. Die Reaktion eignet sich für eine Reihe von Substraten, ist mit funktionellen Gruppen verträglich und ist unter milden, neutralen Bedingungen bequem auszuführen.</description><subject>Activation</subject><subject>Alkine</subject><subject>Asymmetry</subject><subject>Bonding</subject><subject>Chemistry</subject><subject>Demand</subject><subject>Enantiomers</subject><subject>Enantioselektive Synthesen</subject><subject>Fluor</subject><subject>Fluorides</subject><subject>Functional groups</subject><subject>Organokatalysatoren</subject><subject>Silicium</subject><subject>Silicon</subject><subject>Tolerances</subject><subject>YneS protein</subject><issn>0044-8249</issn><issn>1521-3757</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNqFkcFrFDEUh4NYcK1ePQ948TJrkkkmyXFZtqtYt9BWBS8hk0m26abJNJlR5783ZaWIB3t6PN73_XjwA-ANgksEIX6vwt4sMUQtRALzZ2CBKEZ1wyh7DhYQElJzTMQL8DLnWwhhi5lYgHiR9ipErUbl59HpahNUGF3Mxhs9uh-m2k3amzjcOF-uK3-Yw-xVIUIVbdn97KszP8XkepOrlbUx9S7sq_WNS8pXVwc3DKYvsaaeg8mvwIlVPpvXf-Yp-HK2uV5_qM8vth_Xq_NaNy3jNUGc2QbpRjMhmMIdJwwqrHFnGyqattVQUMs14lwzjVpCOtGJvuupVaIztjkF7465Q4r3k8mjvHNZG-9VMHHKEnFMCRWYwIK-_Qe9jVMK5TuJBGwRowKS_1JMIEpJ2_BCLY-UTjHnZKwckrtTaZYIyoeW5ENL8rGlIoij8NN5Mz9By9Vuu_nbrY-uy6P59eiqdJAtK73Lb7ut3H69_H71ebeWn5rf206mCA</recordid><startdate>20160601</startdate><enddate>20160601</enddate><creator>Okusu, Satoshi</creator><creator>Okazaki, Hiroki</creator><creator>Tokunaga, Etsuko</creator><creator>Soloshonok, Vadim A.</creator><creator>Shibata, Norio</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>20160601</creationdate><title>Organocatalytic Enantioselective Nucleophilic Alkynylation of Allyl Fluorides Affording Chiral Skipped Ene-ynes</title><author>Okusu, Satoshi ; Okazaki, Hiroki ; Tokunaga, Etsuko ; Soloshonok, Vadim A. ; Shibata, Norio</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3678-4187f31c3c7997a2b8470a2c2bf359366c095f8c188c7c1644b9b9dbd5fa9bef3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Activation</topic><topic>Alkine</topic><topic>Asymmetry</topic><topic>Bonding</topic><topic>Chemistry</topic><topic>Demand</topic><topic>Enantiomers</topic><topic>Enantioselektive Synthesen</topic><topic>Fluor</topic><topic>Fluorides</topic><topic>Functional groups</topic><topic>Organokatalysatoren</topic><topic>Silicium</topic><topic>Silicon</topic><topic>Tolerances</topic><topic>YneS protein</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Okusu, Satoshi</creatorcontrib><creatorcontrib>Okazaki, Hiroki</creatorcontrib><creatorcontrib>Tokunaga, Etsuko</creatorcontrib><creatorcontrib>Soloshonok, Vadim A.</creatorcontrib><creatorcontrib>Shibata, Norio</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>Okusu, Satoshi</au><au>Okazaki, Hiroki</au><au>Tokunaga, Etsuko</au><au>Soloshonok, Vadim A.</au><au>Shibata, Norio</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Organocatalytic Enantioselective Nucleophilic Alkynylation of Allyl Fluorides Affording Chiral Skipped Ene-ynes</atitle><jtitle>Angewandte Chemie</jtitle><addtitle>Angew. Chem</addtitle><date>2016-06-01</date><risdate>2016</risdate><volume>128</volume><issue>23</issue><spage>6856</spage><epage>6860</epage><pages>6856-6860</pages><issn>0044-8249</issn><eissn>1521-3757</eissn><abstract>Asymmetric methods for preparation of chiral alkynyl‐containing compounds are in extremely high demand in many sectors of chemical research. In this work, we report the discovery of a general organocatalytic enantioselective alkynylation based on the idea of Si/F activation of the allylic C−F bond. This approach features reasonably broad substrate scope, functional group tolerance, and relatively neutral, mild, and operationally convenient reaction conditions; all of which bode well for the synthetic value of the discovered method. In particular, this method provides unique chiral skipped 1,4‐ene‐ynes having two kinds of versatile functional groups.
Nicht konjugiert, dafür chiral: Eine organokatalytische enantioselektive Alkinylierung verläuft unter Si/F‐Aktivierung der allylischen C‐F‐Bindung. Die Reaktion eignet sich für eine Reihe von Substraten, ist mit funktionellen Gruppen verträglich und ist unter milden, neutralen Bedingungen bequem auszuführen.</abstract><cop>Weinheim</cop><pub>Blackwell Publishing Ltd</pub><doi>10.1002/ange.201601928</doi><tpages>5</tpages><oa>free_for_read</oa></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Activation Alkine Asymmetry Bonding Chemistry Demand Enantiomers Enantioselektive Synthesen Fluor Fluorides Functional groups Organokatalysatoren Silicium Silicon Tolerances YneS protein |
| title | Organocatalytic Enantioselective Nucleophilic Alkynylation of Allyl Fluorides Affording Chiral Skipped Ene-ynes |
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