Details

Autor(en) / Beteiligte

• Yang, Junxian
• Zhang, Ji-Wei
• Bao, Wen
• Qiu, Sheng-Qi
• Li, Shaoyu
• Xiang, Shao-Hua
• Song, Jun
• Zhang, Junmin
• Tan, Bin

Titel

Chiral Phosphoric Acid-Catalyzed Remote Control of Axial Chirality at Boron–Carbon Bond

Ist Teil von

• Journal of the American Chemical Society, 2021-08, Vol.143 (33), p.12924-12929

Ort / Verlag

American Chemical Society

Erscheinungsjahr

2021

Link zum Volltext

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• 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.