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
Hauptverfasser: Huang, Gong‐Bin, Huang, Wei‐Hua, Guo, Jing, Xu, Dong‐Liang, Qu, Xiao‐Chen, Zhai, Pei‐Hong, Zheng, Xiu‐Hua, Weng, Jiang, Lu, Gui
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Sprache:eng
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Zusammenfassung: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.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201801446