Asymmetric Allylic Amination of Morita–Baylis–Hillman Carbonates with Silylated tert‐Butylhydroxycarbamate Derivatives
The enantioselective amination of Morita–Baylis–Hillman carbonates with silylated derivatives of tert‐butylhydroxycarbamates using β‐isocupreidine as an organocatalyst was investigated. The corresponding products were obtained in good yields with high enantioselectivities. The scope and limitations...
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| Veröffentlicht in: | European journal of organic chemistry 2017-04, Vol.2017 (14), p.1926-1930 |
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| container_end_page | 1930 |
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| container_issue | 14 |
| container_start_page | 1926 |
| container_title | European journal of organic chemistry |
| container_volume | 2017 |
| creator | Kamlar, Martin Císařová, Ivana Hybelbauerová, Simona Veselý, Jan |
| description | The enantioselective amination of Morita–Baylis–Hillman carbonates with silylated derivatives of tert‐butylhydroxycarbamates using β‐isocupreidine as an organocatalyst was investigated. The corresponding products were obtained in good yields with high enantioselectivities. The scope and limitations of the reported protocol were explored, and representative transformations of the adducts toward heterocyclic compounds were highlighted.
The enantioselective amination of Morita–Baylis–Hillman carbonates with silylated derivatives of tert‐butylhydroxycarbamates by using β‐isocupreidine (β‐ICD) as an organocatalyst is described. The scope and limitations of the reported protocol are outlined, and representative transformations of the adducts toward heterocyclic compounds are highlighted. |
| doi_str_mv | 10.1002/ejoc.201700222 |
| format | Article |
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The enantioselective amination of Morita–Baylis–Hillman carbonates with silylated derivatives of tert‐butylhydroxycarbamates by using β‐isocupreidine (β‐ICD) as an organocatalyst is described. The scope and limitations of the reported protocol are outlined, and representative transformations of the adducts toward heterocyclic compounds are highlighted.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.201700222</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Adducts ; Alkaloids ; Allylic compounds ; Amination ; Asymmetric synthesis ; Asymmetry ; Carbonates ; Derivatives ; Heterocyclic compounds ; Organocatalysis</subject><ispartof>European journal of organic chemistry, 2017-04, Vol.2017 (14), p.1926-1930</ispartof><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-c3452-3aacc5d1a4ad4cbdc532f86b1774fd66250c3992e05ed763a2c33a9ae6243fbe3</citedby><cites>FETCH-LOGICAL-c3452-3aacc5d1a4ad4cbdc532f86b1774fd66250c3992e05ed763a2c33a9ae6243fbe3</cites><orcidid>0000-0001-9115-9858 ; 0000-0003-2535-7260 ; 0000-0001-5198-8950 ; 0000-0002-9612-9831</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%2Fejoc.201700222$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.201700222$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,777,781,1412,27905,27906,45555,45556</link.rule.ids></links><search><creatorcontrib>Kamlar, Martin</creatorcontrib><creatorcontrib>Císařová, Ivana</creatorcontrib><creatorcontrib>Hybelbauerová, Simona</creatorcontrib><creatorcontrib>Veselý, Jan</creatorcontrib><title>Asymmetric Allylic Amination of Morita–Baylis–Hillman Carbonates with Silylated tert‐Butylhydroxycarbamate Derivatives</title><title>European journal of organic chemistry</title><description>The enantioselective amination of Morita–Baylis–Hillman carbonates with silylated derivatives of tert‐butylhydroxycarbamates using β‐isocupreidine as an organocatalyst was investigated. The corresponding products were obtained in good yields with high enantioselectivities. The scope and limitations of the reported protocol were explored, and representative transformations of the adducts toward heterocyclic compounds were highlighted.
The enantioselective amination of Morita–Baylis–Hillman carbonates with silylated derivatives of tert‐butylhydroxycarbamates by using β‐isocupreidine (β‐ICD) as an organocatalyst is described. The scope and limitations of the reported protocol are outlined, and representative transformations of the adducts toward heterocyclic compounds are highlighted.</description><subject>Adducts</subject><subject>Alkaloids</subject><subject>Allylic compounds</subject><subject>Amination</subject><subject>Asymmetric synthesis</subject><subject>Asymmetry</subject><subject>Carbonates</subject><subject>Derivatives</subject><subject>Heterocyclic compounds</subject><subject>Organocatalysis</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqFkT1PwzAQhiMEEqWwMkdiTvFH4tRjGz4KKuoASGyW4ziqqyQuttsSiaE_AYl_2F-CoyLY4Ja70z3vnXRvEJxDMIAAoEu50GKAAEx9g9BB0IOA0ggQCg59HeM4ghS_HAcn1i4AAJQQ2AveR7ata-mMEuGoqtqqy7VquFO6CXUZPmijHN9tP8fcD60vJqqqat6EGTe59qC04Ua5efiovNy3Reikcbvtx3jl2mreFka_tcLDvPbT8Eoatfbr19KeBkclr6w8-8794Pnm-imbRNPZ7V02mkYCxwmKMOdCJAXkMS9ikRciwagckhymaVwWhKAECEwpkiCRRUowRwJjTrkkKMZlLnE_uNjvXRr9upLWsYVemcafZJCi7lsU4D-poY8EIJp6arCnhNHWGlmypVE1Ny2DgHU-sM4H9uODF9C9YKMq2f5Ds-v7Wfar_QL-BZHX</recordid><startdate>20170410</startdate><enddate>20170410</enddate><creator>Kamlar, Martin</creator><creator>Císařová, Ivana</creator><creator>Hybelbauerová, Simona</creator><creator>Veselý, Jan</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0001-9115-9858</orcidid><orcidid>https://orcid.org/0000-0003-2535-7260</orcidid><orcidid>https://orcid.org/0000-0001-5198-8950</orcidid><orcidid>https://orcid.org/0000-0002-9612-9831</orcidid></search><sort><creationdate>20170410</creationdate><title>Asymmetric Allylic Amination of Morita–Baylis–Hillman Carbonates with Silylated tert‐Butylhydroxycarbamate Derivatives</title><author>Kamlar, Martin ; Císařová, Ivana ; Hybelbauerová, Simona ; Veselý, Jan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3452-3aacc5d1a4ad4cbdc532f86b1774fd66250c3992e05ed763a2c33a9ae6243fbe3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Adducts</topic><topic>Alkaloids</topic><topic>Allylic compounds</topic><topic>Amination</topic><topic>Asymmetric synthesis</topic><topic>Asymmetry</topic><topic>Carbonates</topic><topic>Derivatives</topic><topic>Heterocyclic compounds</topic><topic>Organocatalysis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kamlar, Martin</creatorcontrib><creatorcontrib>Císařová, Ivana</creatorcontrib><creatorcontrib>Hybelbauerová, Simona</creatorcontrib><creatorcontrib>Veselý, Jan</creatorcontrib><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kamlar, Martin</au><au>Císařová, Ivana</au><au>Hybelbauerová, Simona</au><au>Veselý, Jan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Asymmetric Allylic Amination of Morita–Baylis–Hillman Carbonates with Silylated tert‐Butylhydroxycarbamate Derivatives</atitle><jtitle>European journal of organic chemistry</jtitle><date>2017-04-10</date><risdate>2017</risdate><volume>2017</volume><issue>14</issue><spage>1926</spage><epage>1930</epage><pages>1926-1930</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>The enantioselective amination of Morita–Baylis–Hillman carbonates with silylated derivatives of tert‐butylhydroxycarbamates using β‐isocupreidine as an organocatalyst was investigated. The corresponding products were obtained in good yields with high enantioselectivities. The scope and limitations of the reported protocol were explored, and representative transformations of the adducts toward heterocyclic compounds were highlighted.
The enantioselective amination of Morita–Baylis–Hillman carbonates with silylated derivatives of tert‐butylhydroxycarbamates by using β‐isocupreidine (β‐ICD) as an organocatalyst is described. The scope and limitations of the reported protocol are outlined, and representative transformations of the adducts toward heterocyclic compounds are highlighted.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ejoc.201700222</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0001-9115-9858</orcidid><orcidid>https://orcid.org/0000-0003-2535-7260</orcidid><orcidid>https://orcid.org/0000-0001-5198-8950</orcidid><orcidid>https://orcid.org/0000-0002-9612-9831</orcidid></addata></record> |
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| identifier | ISSN: 1434-193X |
| ispartof | European journal of organic chemistry, 2017-04, Vol.2017 (14), p.1926-1930 |
| issn | 1434-193X 1099-0690 |
| language | eng |
| recordid | cdi_proquest_journals_1920222903 |
| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Adducts Alkaloids Allylic compounds Amination Asymmetric synthesis Asymmetry Carbonates Derivatives Heterocyclic compounds Organocatalysis |
| title | Asymmetric Allylic Amination of Morita–Baylis–Hillman Carbonates with Silylated tert‐Butylhydroxycarbamate Derivatives |
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