Copper-Catalyzed Borylative Cross-Coupling of Allenes and Imines: Selective Three-Component Assembly of Branched Homoallyl Amines
A copper‐catalyzed three‐component coupling of allenes, bis(pinacolato)diboron, and imines allows regio‐, chemo‐, and diastereoselective assembly of branched α,β‐substituted‐γ‐boryl homoallylic amines, that is, products bearing versatile amino, alkenyl, and borane functionality. Alternatively, conve...
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| Veröffentlicht in: | Angewandte Chemie 2016-01, Vol.128 (3), p.1114-1119 |
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| creator | Rae, James Yeung, Kay McDouall, Joseph J. W. Procter, David J. |
| description | A copper‐catalyzed three‐component coupling of allenes, bis(pinacolato)diboron, and imines allows regio‐, chemo‐, and diastereoselective assembly of branched α,β‐substituted‐γ‐boryl homoallylic amines, that is, products bearing versatile amino, alkenyl, and borane functionality. Alternatively, convenient oxidative workup allows access to α‐substituted‐β‐amino ketones. A computational study has been used to probe the stereochemical course of the cross‐coupling.
Ein Triumvirat: Dreikomponentenkupplungen von Allenen, B2pin2 und Iminen führen zu funktionalisierten Homoallylaminen oder – nach Oxidation – zu Mannich‐Produkten. Der Prozess nutzt einen käuflichen Kupferkatalysator, eignet sich für viele Allene und Imine und ergibt die komplexen Produkte regio‐ und diastereokontrolliert in hohen Ausbeuten. Der stereochemische Verlauf der Kreuzkupplung wurde mithilfe von Rechnungen untersucht. |
| doi_str_mv | 10.1002/ange.201508959 |
| format | Article |
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Ein Triumvirat: Dreikomponentenkupplungen von Allenen, B2pin2 und Iminen führen zu funktionalisierten Homoallylaminen oder – nach Oxidation – zu Mannich‐Produkten. Der Prozess nutzt einen käuflichen Kupferkatalysator, eignet sich für viele Allene und Imine und ergibt die komplexen Produkte regio‐ und diastereokontrolliert in hohen Ausbeuten. Der stereochemische Verlauf der Kreuzkupplung wurde mithilfe von Rechnungen untersucht.</description><identifier>ISSN: 0044-8249</identifier><identifier>EISSN: 1521-3757</identifier><identifier>DOI: 10.1002/ange.201508959</identifier><language>eng</language><publisher>Weinheim: Blackwell Publishing Ltd</publisher><subject>Allene ; Amines ; Assembly ; Bearing ; Bor ; Boranes ; Branched ; Chemistry ; Computer applications ; Copper ; Coupling ; Cross coupling ; Imine ; Imines ; Joining ; Ketones ; Kreuzkupplungen ; Kupfer</subject><ispartof>Angewandte Chemie, 2016-01, Vol.128 (3), p.1114-1119</ispartof><rights>2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.</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-c3679-42e9b141a6bcfb76cf14a1a2127d5527ca07231261e6618f5afe80d0dc9ab3f93</citedby><cites>FETCH-LOGICAL-c3679-42e9b141a6bcfb76cf14a1a2127d5527ca07231261e6618f5afe80d0dc9ab3f93</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.201508959$$EPDF$$P50$$Gwiley$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fange.201508959$$EHTML$$P50$$Gwiley$$Hfree_for_read</linktohtml><link.rule.ids>314,776,780,1411,27903,27904,45553,45554</link.rule.ids></links><search><creatorcontrib>Rae, James</creatorcontrib><creatorcontrib>Yeung, Kay</creatorcontrib><creatorcontrib>McDouall, Joseph J. W.</creatorcontrib><creatorcontrib>Procter, David J.</creatorcontrib><title>Copper-Catalyzed Borylative Cross-Coupling of Allenes and Imines: Selective Three-Component Assembly of Branched Homoallyl Amines</title><title>Angewandte Chemie</title><addtitle>Angew. Chem</addtitle><description>A copper‐catalyzed three‐component coupling of allenes, bis(pinacolato)diboron, and imines allows regio‐, chemo‐, and diastereoselective assembly of branched α,β‐substituted‐γ‐boryl homoallylic amines, that is, products bearing versatile amino, alkenyl, and borane functionality. Alternatively, convenient oxidative workup allows access to α‐substituted‐β‐amino ketones. A computational study has been used to probe the stereochemical course of the cross‐coupling.
Ein Triumvirat: Dreikomponentenkupplungen von Allenen, B2pin2 und Iminen führen zu funktionalisierten Homoallylaminen oder – nach Oxidation – zu Mannich‐Produkten. Der Prozess nutzt einen käuflichen Kupferkatalysator, eignet sich für viele Allene und Imine und ergibt die komplexen Produkte regio‐ und diastereokontrolliert in hohen Ausbeuten. Der stereochemische Verlauf der Kreuzkupplung wurde mithilfe von Rechnungen untersucht.</description><subject>Allene</subject><subject>Amines</subject><subject>Assembly</subject><subject>Bearing</subject><subject>Bor</subject><subject>Boranes</subject><subject>Branched</subject><subject>Chemistry</subject><subject>Computer applications</subject><subject>Copper</subject><subject>Coupling</subject><subject>Cross coupling</subject><subject>Imine</subject><subject>Imines</subject><subject>Joining</subject><subject>Ketones</subject><subject>Kreuzkupplungen</subject><subject>Kupfer</subject><issn>0044-8249</issn><issn>1521-3757</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><recordid>eNqFkjFv1DAYhiMEEkfpyhyJhSWHPye2Y7Y0KteqVUGihdFynC9tihMHO9cSNv45vh6qEANM9vA8r6z3dZK8ArIGQuhbPV7jmhJgpJRMPklWwChkuWDiabIipCiykhbyefIihFtCCKdCrpKftZsm9FmtZ22XH9imR84vVs_9Haa1dyFktdtOth-vU9ellbU4Ykj12KanQx-v79JPaNE88Jc3HjHyw-RGHOe0CgGHxi4788jr0dzE_BM3OG3tYtPqIeBl8qzTNuDh7_MguXp_fFmfZOcfNqd1dZ6ZnAuZFRRlAwVo3piuEdx0UGjQFKhoGaPCaCJoDpQDcg5lx3SHJWlJa6Ru8k7mB8mbfe7k3bcthlkNfTBorR7RbYOCMnZUllzyiL7-C711Wz_G1ymQsUgJObB_UoKxkgsuRaTWe8rsyvTYqcn3g_aLAqJ2u6ndbupxtyjIvXDfW1z-Q6vqYnP8p5vt3T7M-P3R1f6r4iL-BPXlYqOIOCNn8PGzkvkvBQarTw</recordid><startdate>20160118</startdate><enddate>20160118</enddate><creator>Rae, James</creator><creator>Yeung, Kay</creator><creator>McDouall, Joseph J. 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W. ; Procter, David J.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3679-42e9b141a6bcfb76cf14a1a2127d5527ca07231261e6618f5afe80d0dc9ab3f93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Allene</topic><topic>Amines</topic><topic>Assembly</topic><topic>Bearing</topic><topic>Bor</topic><topic>Boranes</topic><topic>Branched</topic><topic>Chemistry</topic><topic>Computer applications</topic><topic>Copper</topic><topic>Coupling</topic><topic>Cross coupling</topic><topic>Imine</topic><topic>Imines</topic><topic>Joining</topic><topic>Ketones</topic><topic>Kreuzkupplungen</topic><topic>Kupfer</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Rae, James</creatorcontrib><creatorcontrib>Yeung, Kay</creatorcontrib><creatorcontrib>McDouall, Joseph J. W.</creatorcontrib><creatorcontrib>Procter, David J.</creatorcontrib><collection>Istex</collection><collection>Wiley Online Library Open Access</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>Rae, James</au><au>Yeung, Kay</au><au>McDouall, Joseph J. W.</au><au>Procter, David J.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Copper-Catalyzed Borylative Cross-Coupling of Allenes and Imines: Selective Three-Component Assembly of Branched Homoallyl Amines</atitle><jtitle>Angewandte Chemie</jtitle><addtitle>Angew. Chem</addtitle><date>2016-01-18</date><risdate>2016</risdate><volume>128</volume><issue>3</issue><spage>1114</spage><epage>1119</epage><pages>1114-1119</pages><issn>0044-8249</issn><eissn>1521-3757</eissn><abstract>A copper‐catalyzed three‐component coupling of allenes, bis(pinacolato)diboron, and imines allows regio‐, chemo‐, and diastereoselective assembly of branched α,β‐substituted‐γ‐boryl homoallylic amines, that is, products bearing versatile amino, alkenyl, and borane functionality. Alternatively, convenient oxidative workup allows access to α‐substituted‐β‐amino ketones. A computational study has been used to probe the stereochemical course of the cross‐coupling.
Ein Triumvirat: Dreikomponentenkupplungen von Allenen, B2pin2 und Iminen führen zu funktionalisierten Homoallylaminen oder – nach Oxidation – zu Mannich‐Produkten. Der Prozess nutzt einen käuflichen Kupferkatalysator, eignet sich für viele Allene und Imine und ergibt die komplexen Produkte regio‐ und diastereokontrolliert in hohen Ausbeuten. Der stereochemische Verlauf der Kreuzkupplung wurde mithilfe von Rechnungen untersucht.</abstract><cop>Weinheim</cop><pub>Blackwell Publishing Ltd</pub><doi>10.1002/ange.201508959</doi><tpages>6</tpages><oa>free_for_read</oa></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Allene Amines Assembly Bearing Bor Boranes Branched Chemistry Computer applications Copper Coupling Cross coupling Imine Imines Joining Ketones Kreuzkupplungen Kupfer |
| title | Copper-Catalyzed Borylative Cross-Coupling of Allenes and Imines: Selective Three-Component Assembly of Branched Homoallyl Amines |
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