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• W3191230491 abstract "The previously elusive catalytic enantioselective construction of axially chiral B-aryl-1,2-azaborines with a C-B stereogenic axis has been realized through a chiral phosphoric acid-catalyzed desymmetrization strategy reported herein. The electrophilic aromatic substitution reaction of 3,5-disubsituted phenols with diazodicarboxamides could afford these axially chiral structures in good efficiency with excellent enantiocontrol. The efficient long-range stereochemical control is achieved by multiple well-defined H-bonding interactions between chiral phosphoric acid and both substrates. Meanwhile, the reaction duration could be markedly shortened with weakly acidic N-H in 1,2-azaborine acting as H-bond donor. The scalability of the reaction and facile cleavage of the N-N bond in the product further demonstrated the practicality of this method." @default.
• W3191230491 created "2021-08-16" @default.
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• W3191230491 date "2021-08-12" @default.
• W3191230491 modified "2023-10-16" @default.
• W3191230491 title "Chiral Phosphoric Acid-Catalyzed Remote Control of Axial Chirality at Boron–Carbon Bond" @default.
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• W3191230491 doi "https://doi.org/10.1021/jacs.1c05079" @default.
• W3191230491 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/34384026" @default.
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