Enantioselective Synthesis of Triarylmethanes via Organocatalytic 1,6‐Addition of Arylboronic Acids to para‐Quinone Methides
A method for the preparation of chiral triarylmethanes via organocatalytic 1,6‐addition of arylboronic acids to para‐quinone methides (p‐QMs) was established. Here the use of salicylaldehyde‐derived p‐QMs with an ortho‐hydroxy substituent as a directing group was essential for the remote stereocontr...
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| Veröffentlicht in: | Advanced synthesis & catalysis 2019-03, Vol.361 (6), p.1241-1246 |
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| container_issue | 6 |
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| container_title | Advanced synthesis & catalysis |
| container_volume | 361 |
| creator | Huang, Gong‐Bin Huang, Wei‐Hua Guo, Jing Xu, Dong‐Liang Qu, Xiao‐Chen Zhai, Pei‐Hong Zheng, Xiu‐Hua Weng, Jiang Lu, Gui |
| description | A method for the preparation of chiral triarylmethanes via organocatalytic 1,6‐addition of arylboronic acids to para‐quinone methides (p‐QMs) was established. Here the use of salicylaldehyde‐derived p‐QMs with an ortho‐hydroxy substituent as a directing group was essential for the remote stereocontrol. In the presence of a BINOL catalyst, chiral triarylmethanes can be obtained in high yields (up to 99%) with excellent enantioselectivities (up to 99% ee). This method shows broad substrate tolerance and can be easily scaled up, both electron‐rich and electron‐deficient arylboronic acids are suitable substrates for this addition reaction. |
| doi_str_mv | 10.1002/adsc.201801446 |
| format | Article |
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Here the use of salicylaldehyde‐derived p‐QMs with an ortho‐hydroxy substituent as a directing group was essential for the remote stereocontrol. In the presence of a BINOL catalyst, chiral triarylmethanes can be obtained in high yields (up to 99%) with excellent enantioselectivities (up to 99% ee). This method shows broad substrate tolerance and can be easily scaled up, both electron‐rich and electron‐deficient arylboronic acids are suitable substrates for this addition reaction.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.201801446</identifier><language>eng</language><publisher>Heidelberg: Wiley Subscription Services, Inc</publisher><subject>arylboronic acids ; asymmetric catalysis ; Enantiomers ; quinone methides ; Substrates ; synthetic methods ; triarylmethane</subject><ispartof>Advanced synthesis & catalysis, 2019-03, Vol.361 (6), p.1241-1246</ispartof><rights>2019 Wiley‐VCH Verlag GmbH & Co. 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Here the use of salicylaldehyde‐derived p‐QMs with an ortho‐hydroxy substituent as a directing group was essential for the remote stereocontrol. In the presence of a BINOL catalyst, chiral triarylmethanes can be obtained in high yields (up to 99%) with excellent enantioselectivities (up to 99% ee). This method shows broad substrate tolerance and can be easily scaled up, both electron‐rich and electron‐deficient arylboronic acids are suitable substrates for this addition reaction.</description><subject>arylboronic acids</subject><subject>asymmetric catalysis</subject><subject>Enantiomers</subject><subject>quinone methides</subject><subject>Substrates</subject><subject>synthetic methods</subject><subject>triarylmethane</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNqFkMtOAyEYhYnRxFrduiZxayswN1hOar0kNY1pXROGYSzNFCrQmtn1EXxGn0Samrp0A_w55zt_OABcYzTECJE7UXs5JAhThNM0PwE9nONskOKcnR7fGToHF94vEcIFLYoe2I2NMEFbr1olg94qOOtMWCivPbQNnDstXNeuVFgIozzcagGn7l0YK0UQbRe0hPg2_959lXWtY47ZU2VEKuusiWopde1hsHAtnIi-14021ij4EiN1rfwlOGtE69XV790Hbw_j-ehpMJk-Po_KyUAmWZoPKlEkrG7qPA6Ipbgo6gw1WZ5KVlTxICoTQsZfVinNmGyqqJKCEUQpUZTRpA9uDrlrZz82yge-tBtn4kpOMMMJIjTB0TU8uKSz3jvV8LXTq1gBx4jvW-b7lvmx5QiwA_CpW9X94-bl_Wz0x_4AwjqEJw</recordid><startdate>20190315</startdate><enddate>20190315</enddate><creator>Huang, Gong‐Bin</creator><creator>Huang, Wei‐Hua</creator><creator>Guo, Jing</creator><creator>Xu, Dong‐Liang</creator><creator>Qu, Xiao‐Chen</creator><creator>Zhai, Pei‐Hong</creator><creator>Zheng, Xiu‐Hua</creator><creator>Weng, Jiang</creator><creator>Lu, Gui</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>20190315</creationdate><title>Enantioselective Synthesis of Triarylmethanes via Organocatalytic 1,6‐Addition of Arylboronic Acids to para‐Quinone Methides</title><author>Huang, Gong‐Bin ; Huang, Wei‐Hua ; Guo, Jing ; Xu, Dong‐Liang ; Qu, Xiao‐Chen ; Zhai, Pei‐Hong ; Zheng, Xiu‐Hua ; Weng, Jiang ; Lu, Gui</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3546-ba739dfd6546094177d50f564c97b4c92e5aac161b4859cfb50f27920882e8983</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>arylboronic acids</topic><topic>asymmetric catalysis</topic><topic>Enantiomers</topic><topic>quinone methides</topic><topic>Substrates</topic><topic>synthetic methods</topic><topic>triarylmethane</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Huang, Gong‐Bin</creatorcontrib><creatorcontrib>Huang, Wei‐Hua</creatorcontrib><creatorcontrib>Guo, Jing</creatorcontrib><creatorcontrib>Xu, Dong‐Liang</creatorcontrib><creatorcontrib>Qu, Xiao‐Chen</creatorcontrib><creatorcontrib>Zhai, Pei‐Hong</creatorcontrib><creatorcontrib>Zheng, Xiu‐Hua</creatorcontrib><creatorcontrib>Weng, Jiang</creatorcontrib><creatorcontrib>Lu, Gui</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>Huang, Gong‐Bin</au><au>Huang, Wei‐Hua</au><au>Guo, Jing</au><au>Xu, Dong‐Liang</au><au>Qu, Xiao‐Chen</au><au>Zhai, Pei‐Hong</au><au>Zheng, Xiu‐Hua</au><au>Weng, Jiang</au><au>Lu, Gui</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enantioselective Synthesis of Triarylmethanes via Organocatalytic 1,6‐Addition of Arylboronic Acids to para‐Quinone Methides</atitle><jtitle>Advanced synthesis & catalysis</jtitle><date>2019-03-15</date><risdate>2019</risdate><volume>361</volume><issue>6</issue><spage>1241</spage><epage>1246</epage><pages>1241-1246</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>A method for the preparation of chiral triarylmethanes via organocatalytic 1,6‐addition of arylboronic acids to para‐quinone methides (p‐QMs) was established. Here the use of salicylaldehyde‐derived p‐QMs with an ortho‐hydroxy substituent as a directing group was essential for the remote stereocontrol. In the presence of a BINOL catalyst, chiral triarylmethanes can be obtained in high yields (up to 99%) with excellent enantioselectivities (up to 99% ee). This method shows broad substrate tolerance and can be easily scaled up, both electron‐rich and electron‐deficient arylboronic acids are suitable substrates for this addition reaction.</abstract><cop>Heidelberg</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/adsc.201801446</doi><tpages>6</tpages></addata></record> |
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| subjects | arylboronic acids asymmetric catalysis Enantiomers quinone methides Substrates synthetic methods triarylmethane |
| title | Enantioselective Synthesis of Triarylmethanes via Organocatalytic 1,6‐Addition of Arylboronic Acids to para‐Quinone Methides |
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