Chiral Carborane Acids Decorated with Binol-Based Phosphonates: Synthesis, Characterization, and Application.
Hua-Jie JiangHonghua ZuoMin ZhuIllia SharanovElisabeth IrranHendrik F T KlareSofja TshepelevitshMärt LõkovIvo LeitoMartin OestreichPublished in: The Journal of organic chemistry (2023)
The syntheses of hexabrominated closo -carborates decorated with different chiral Binol-derived phosphonates and their conjugate acids are described. X-ray diffraction analysis reveals a polymeric structure for the sodium salt with the anionic units connected by [B-Br-Na-O═P] + linkages. For the acid, coordination of the proton to the phosphonate's P═O oxygen atom is assumed. The p K a value was estimated by combining experiments and computations. Application of these Brønsted acids as chiral catalysts in an imino-ene and a Mukaiyama-Mannich reaction was moderately successful.
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