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Isothiourea-Catalyzed Acylative Desymmetrization of Silicon-Centered Bisphenols.

Xuanlong LiaoHongwei ZhouXingkuan ChenJianfeng Xu
Published in: Organic letters (2023)
The preparation of optically pure organosilicon compounds bearing a stereogenic center at the silicon atom is an attractive but challenging enterprise. Herein we disclose an isothiourea (ITU)-catalyzed monoacylation reaction of silicon-centered bisphenols with 2,2-diphenylacetic pivalic anhydride, delivering tetrasubstituted organosilanes in moderate to excellent yields (36-91%) with moderate to excellent enantiomeric ratios (68:32-97.5:2.5). This organocatalytic desymmetrization approach can be performed on gram scale, and the products can be converted to other valuable compounds.
Keyphrases
  • room temperature
  • high intensity
  • gram negative
  • mass spectrometry
  • molecularly imprinted
  • high resolution
  • capillary electrophoresis