Enantioselective Copper‐Catalyzed Three‐Component Carboboronation of Allenes: Access to Functionalized Dibenzo [b,f][1,4]oxazepine Derivatives
A copper‐catalyzed enantioselective three‐component difunctionalization of allenes with seven‐membered cyclic imines and bis(pinacolato)diboron (B2(Pin)2) to approach functionalized dibenzo[b,f][1,4]oxazepine derivatives is developed. The chiral products are obtained in up to 81% yield, >20:1 dr,...
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| Veröffentlicht in: | Advanced synthesis & catalysis 2019-08, Vol.361 (15), p.3582-3587 |
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| container_title | Advanced synthesis & catalysis |
| container_volume | 361 |
| creator | Deng, Hao Meng, Ziwei Wang, Sifan Zhang, Zheming Zhang, Yaqi Shangguan, Yu Yang, Fazhou Yuan, Dekai Guo, Hongchao Zhang, Cheng |
| description | A copper‐catalyzed enantioselective three‐component difunctionalization of allenes with seven‐membered cyclic imines and bis(pinacolato)diboron (B2(Pin)2) to approach functionalized dibenzo[b,f][1,4]oxazepine derivatives is developed. The chiral products are obtained in up to 81% yield, >20:1 dr, and 98% ee when either a chiral diphosphine ligand or a chiral ferrocenyl‐based P,N‐ligand is used. Furthermore, the reaction exhibits reversed diastereoselectivities when the chiral diphosphine ligand and the chiral P,N‐ligand are used respectively. |
| doi_str_mv | 10.1002/adsc.201900503 |
| format | Article |
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The chiral products are obtained in up to 81% yield, >20:1 dr, and 98% ee when either a chiral diphosphine ligand or a chiral ferrocenyl‐based P,N‐ligand is used. Furthermore, the reaction exhibits reversed diastereoselectivities when the chiral diphosphine ligand and the chiral P,N‐ligand are used respectively.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.201900503</identifier><language>eng</language><publisher>Heidelberg: Wiley Subscription Services, Inc</publisher><subject>asymmetric catalysis ; boron ; Copper ; copper-catalyzed ; cross-coupling ; Derivatives ; difunctionalization of allenes ; Enantiomers ; Imines ; Ligands</subject><ispartof>Advanced synthesis & catalysis, 2019-08, Vol.361 (15), p.3582-3587</ispartof><rights>2019 Wiley‐VCH Verlag GmbH & Co. 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The chiral products are obtained in up to 81% yield, >20:1 dr, and 98% ee when either a chiral diphosphine ligand or a chiral ferrocenyl‐based P,N‐ligand is used. Furthermore, the reaction exhibits reversed diastereoselectivities when the chiral diphosphine ligand and the chiral P,N‐ligand are used respectively.</description><subject>asymmetric catalysis</subject><subject>boron</subject><subject>Copper</subject><subject>copper-catalyzed</subject><subject>cross-coupling</subject><subject>Derivatives</subject><subject>difunctionalization of allenes</subject><subject>Enantiomers</subject><subject>Imines</subject><subject>Ligands</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNqFkM1Kw0AUhYMoWKtb1wNu2zo_mUzHXUlbFQourKtSwmRygynpTJxJq-3KRxAf0ScxoaJLV_dy7_kOhxMElwQPCMb0WmVeDygmEmOO2VHQIRHh_ZBE8vh35_g0OPN-hTERQyE6wefEKFMX1kMJui62gGJbVeC-3j9iVatyt4cMzZ8dQHux68oaMDWKlUttap01qoENsjkalSUY8DdopDV4j2qLphuj27cqi9ZmXKRg9hYt0l6-XJBeuLRvag9VYQCNwRVb1Qbw58FJrkoPFz-zGzxNJ_P4rj97uL2PR7O-Dilm_aFICYsoI5RhkWstWS6yPMM8lTqnIWWCcy65EFxHjGZA0zACDpIQhrnMKOsGVwffytmXDfg6WdmNa8L6hNJoSHk0lKxRDQ4q7az3DvKkcsVauV1CcNL2nrS9J7-9N4A8AK9FCbt_1Mlo_Bj_sd8fa4p6</recordid><startdate>20190805</startdate><enddate>20190805</enddate><creator>Deng, Hao</creator><creator>Meng, Ziwei</creator><creator>Wang, Sifan</creator><creator>Zhang, Zheming</creator><creator>Zhang, Yaqi</creator><creator>Shangguan, Yu</creator><creator>Yang, Fazhou</creator><creator>Yuan, Dekai</creator><creator>Guo, Hongchao</creator><creator>Zhang, Cheng</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20190805</creationdate><title>Enantioselective Copper‐Catalyzed Three‐Component Carboboronation of Allenes: Access to Functionalized Dibenzo [b,f][1,4]oxazepine Derivatives</title><author>Deng, Hao ; Meng, Ziwei ; Wang, Sifan ; Zhang, Zheming ; Zhang, Yaqi ; Shangguan, Yu ; Yang, Fazhou ; Yuan, Dekai ; Guo, Hongchao ; Zhang, Cheng</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4203-87b1362312307fcc93f7dfd05b9cf2423755595775c632de2b46e5e9113059d23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>asymmetric catalysis</topic><topic>boron</topic><topic>Copper</topic><topic>copper-catalyzed</topic><topic>cross-coupling</topic><topic>Derivatives</topic><topic>difunctionalization of allenes</topic><topic>Enantiomers</topic><topic>Imines</topic><topic>Ligands</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Deng, Hao</creatorcontrib><creatorcontrib>Meng, Ziwei</creatorcontrib><creatorcontrib>Wang, Sifan</creatorcontrib><creatorcontrib>Zhang, Zheming</creatorcontrib><creatorcontrib>Zhang, Yaqi</creatorcontrib><creatorcontrib>Shangguan, Yu</creatorcontrib><creatorcontrib>Yang, Fazhou</creatorcontrib><creatorcontrib>Yuan, Dekai</creatorcontrib><creatorcontrib>Guo, Hongchao</creatorcontrib><creatorcontrib>Zhang, Cheng</creatorcontrib><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Advanced synthesis & catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Deng, Hao</au><au>Meng, Ziwei</au><au>Wang, Sifan</au><au>Zhang, Zheming</au><au>Zhang, Yaqi</au><au>Shangguan, Yu</au><au>Yang, Fazhou</au><au>Yuan, Dekai</au><au>Guo, Hongchao</au><au>Zhang, Cheng</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enantioselective Copper‐Catalyzed Three‐Component Carboboronation of Allenes: Access to Functionalized Dibenzo [b,f][1,4]oxazepine Derivatives</atitle><jtitle>Advanced synthesis & catalysis</jtitle><date>2019-08-05</date><risdate>2019</risdate><volume>361</volume><issue>15</issue><spage>3582</spage><epage>3587</epage><pages>3582-3587</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>A copper‐catalyzed enantioselective three‐component difunctionalization of allenes with seven‐membered cyclic imines and bis(pinacolato)diboron (B2(Pin)2) to approach functionalized dibenzo[b,f][1,4]oxazepine derivatives is developed. The chiral products are obtained in up to 81% yield, >20:1 dr, and 98% ee when either a chiral diphosphine ligand or a chiral ferrocenyl‐based P,N‐ligand is used. Furthermore, the reaction exhibits reversed diastereoselectivities when the chiral diphosphine ligand and the chiral P,N‐ligand are used respectively.</abstract><cop>Heidelberg</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/adsc.201900503</doi><tpages>6</tpages></addata></record> |
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| subjects | asymmetric catalysis boron Copper copper-catalyzed cross-coupling Derivatives difunctionalization of allenes Enantiomers Imines Ligands |
| title | Enantioselective Copper‐Catalyzed Three‐Component Carboboronation of Allenes: Access to Functionalized Dibenzo [b,f][1,4]oxazepine Derivatives |
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