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Huang, Gong‐Bin; Huang, Wei‐Hua; Guo, Jing; Xu, Dong‐Liang; Qu, Xiao‐Chen; Zhai, Pei‐Hong; Zheng, Xiu‐Hua; Weng, Jiang; Lu, Gui
Advanced synthesis & catalysis, March 15, 2019, Letnik: 361, Številka: 6Journal Article
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.
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