Copper(I)‐Catalyzed Enantio‐ and Diastereodivergent Borylative Coupling of Styrenes and Imines
We report copper(I)‐catalyzed enantio‐ and diastereodivergent borylative coupling of styrenes and imines to produce enantiomerically‐enriched α,β‐dibranched γ‐boryl amine derivatives. Each of the four possible stereoisomers of the products, derived from the two contiguous stereocenters, was selectiv...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2018-07, Vol.57 (27), p.8265-8269 |
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| creator | Itoh, Taisuke Kanzaki, Yamato Shimizu, Yohei Kanai, Motomu |
| description | We report copper(I)‐catalyzed enantio‐ and diastereodivergent borylative coupling of styrenes and imines to produce enantiomerically‐enriched α,β‐dibranched γ‐boryl amine derivatives. Each of the four possible stereoisomers of the products, derived from the two contiguous stereocenters, was selectively accessible by choosing a proper chiral ligand for the copper catalyst. This method, which combines catalyst‐controlled stereodivergency and constitutional divergency derived from the lynchpin motif (i.e., the C−B bond), offers a strategy for addressing the construction of molecular structural diversity concomitant with precise chirality control.
Molecular synthesis on demand: Diastereodivergent, enantioselective borylative coupling between styrenes and aldimines using copper(I) catalysis is reported. By combining catalyst‐controlled stereodivergency and C−B bond‐derived constitutional divergency, a wide range of amine derivatives can be synthesized with precise chirality control. |
| doi_str_mv | 10.1002/anie.201804117 |
| format | Article |
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Molecular synthesis on demand: Diastereodivergent, enantioselective borylative coupling between styrenes and aldimines using copper(I) catalysis is reported. By combining catalyst‐controlled stereodivergency and C−B bond‐derived constitutional divergency, a wide range of amine derivatives can be synthesized with precise chirality control.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201804117</identifier><identifier>PMID: 29709090</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>asymmetric catalysis ; borylation ; Catalysis ; Catalysts ; chiral amines ; Chirality ; Copper ; Coupling (molecular) ; difunctionalization ; Imines ; Molecular chains ; stereodivergent reaction ; Stereoisomers ; Styrenes</subject><ispartof>Angewandte Chemie International Edition, 2018-07, Vol.57 (27), p.8265-8269</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-c4767-f0216889c94cd3eec3d66137e2fac55dc510886defd0543debebefd76d3deb063</citedby><cites>FETCH-LOGICAL-c4767-f0216889c94cd3eec3d66137e2fac55dc510886defd0543debebefd76d3deb063</cites><orcidid>0000-0003-1977-7648</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.201804117$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201804117$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>315,781,785,1418,27929,27930,45579,45580</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/29709090$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Itoh, Taisuke</creatorcontrib><creatorcontrib>Kanzaki, Yamato</creatorcontrib><creatorcontrib>Shimizu, Yohei</creatorcontrib><creatorcontrib>Kanai, Motomu</creatorcontrib><title>Copper(I)‐Catalyzed Enantio‐ and Diastereodivergent Borylative Coupling of Styrenes and Imines</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>We report copper(I)‐catalyzed enantio‐ and diastereodivergent borylative coupling of styrenes and imines to produce enantiomerically‐enriched α,β‐dibranched γ‐boryl amine derivatives. Each of the four possible stereoisomers of the products, derived from the two contiguous stereocenters, was selectively accessible by choosing a proper chiral ligand for the copper catalyst. This method, which combines catalyst‐controlled stereodivergency and constitutional divergency derived from the lynchpin motif (i.e., the C−B bond), offers a strategy for addressing the construction of molecular structural diversity concomitant with precise chirality control.
Molecular synthesis on demand: Diastereodivergent, enantioselective borylative coupling between styrenes and aldimines using copper(I) catalysis is reported. By combining catalyst‐controlled stereodivergency and C−B bond‐derived constitutional divergency, a wide range of amine derivatives can be synthesized with precise chirality control.</description><subject>asymmetric catalysis</subject><subject>borylation</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>chiral amines</subject><subject>Chirality</subject><subject>Copper</subject><subject>Coupling (molecular)</subject><subject>difunctionalization</subject><subject>Imines</subject><subject>Molecular chains</subject><subject>stereodivergent reaction</subject><subject>Stereoisomers</subject><subject>Styrenes</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNqFkLtOxDAQRS0E4t1Sokg0S5HFj8ROSggLrISgAOrIG0-QUdYOdgIKFZ_AN_IleFkeEg2aYu6MzlyNLkJ7BI8JxvRIGg1jikmGE0LECtokKSUxE4KtBp0wFossJRtoy_uHwGcZ5utog-YC56E20aywbQtuND18f30rZCeb4QVUNDHSdNqGXSSNik619B04sEo_gbsH00Un1g2N7MIcFbZvG23uI1tHN93gwID_PJvOdZA7aK2WjYfdr76N7s4mt8VFfHl9Pi2OL-MqEVzENaaEZ1le5UmlGEDFFOeECaC1rNJUVSnBWcYV1AqnCVMwC1UrwdVCY8620Wjp2zr72IPvyrn2FTSNNGB7X1LMGMsxT3BAD_6gD7Z3JnwXqDQnjJKEBmq8pCpnvXdQl63Tc-mGkuBykX65SL_8ST8c7H_Z9rM5qB_8O-4A5EvgWTcw_GNXHl9NJ7_mHwMck4I</recordid><startdate>20180702</startdate><enddate>20180702</enddate><creator>Itoh, Taisuke</creator><creator>Kanzaki, Yamato</creator><creator>Shimizu, Yohei</creator><creator>Kanai, Motomu</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/0000-0003-1977-7648</orcidid></search><sort><creationdate>20180702</creationdate><title>Copper(I)‐Catalyzed Enantio‐ and Diastereodivergent Borylative Coupling of Styrenes and Imines</title><author>Itoh, Taisuke ; Kanzaki, Yamato ; Shimizu, Yohei ; Kanai, Motomu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4767-f0216889c94cd3eec3d66137e2fac55dc510886defd0543debebefd76d3deb063</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>asymmetric catalysis</topic><topic>borylation</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>chiral amines</topic><topic>Chirality</topic><topic>Copper</topic><topic>Coupling (molecular)</topic><topic>difunctionalization</topic><topic>Imines</topic><topic>Molecular chains</topic><topic>stereodivergent reaction</topic><topic>Stereoisomers</topic><topic>Styrenes</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Itoh, Taisuke</creatorcontrib><creatorcontrib>Kanzaki, Yamato</creatorcontrib><creatorcontrib>Shimizu, Yohei</creatorcontrib><creatorcontrib>Kanai, Motomu</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>Itoh, Taisuke</au><au>Kanzaki, Yamato</au><au>Shimizu, Yohei</au><au>Kanai, Motomu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Copper(I)‐Catalyzed Enantio‐ and Diastereodivergent Borylative Coupling of Styrenes and Imines</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2018-07-02</date><risdate>2018</risdate><volume>57</volume><issue>27</issue><spage>8265</spage><epage>8269</epage><pages>8265-8269</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>We report copper(I)‐catalyzed enantio‐ and diastereodivergent borylative coupling of styrenes and imines to produce enantiomerically‐enriched α,β‐dibranched γ‐boryl amine derivatives. Each of the four possible stereoisomers of the products, derived from the two contiguous stereocenters, was selectively accessible by choosing a proper chiral ligand for the copper catalyst. This method, which combines catalyst‐controlled stereodivergency and constitutional divergency derived from the lynchpin motif (i.e., the C−B bond), offers a strategy for addressing the construction of molecular structural diversity concomitant with precise chirality control.
Molecular synthesis on demand: Diastereodivergent, enantioselective borylative coupling between styrenes and aldimines using copper(I) catalysis is reported. By combining catalyst‐controlled stereodivergency and C−B bond‐derived constitutional divergency, a wide range of amine derivatives can be synthesized with precise chirality control.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>29709090</pmid><doi>10.1002/anie.201804117</doi><tpages>5</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0003-1977-7648</orcidid></addata></record> |
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| subjects | asymmetric catalysis borylation Catalysis Catalysts chiral amines Chirality Copper Coupling (molecular) difunctionalization Imines Molecular chains stereodivergent reaction Stereoisomers Styrenes |
| title | Copper(I)‐Catalyzed Enantio‐ and Diastereodivergent Borylative Coupling of Styrenes and Imines |
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