4.7 Article

Halohydroxylation of alkenyl MIDA boronates: switchable stereoselectivity induced by B(MIDA) substituent

Journal

CHEMICAL COMMUNICATIONS
Volume 56, Issue 31, Pages 4332-4335

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d0cc00722f

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Funding

  1. National Natural Science Foundation of China [21971261]
  2. ``Double First-Class'' Discipline Construction Foundation of the University of South China [2017SYL06]
  3. Foundation of Hu'nan Educational Committee [18C0476]

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The synthesis of alpha-boryl halohydrins via difunctionalization of alkenyl MIDA boronates has been reported. Intriguing stereoselectivity was found with different halogen sources, which arises from the special stabilizing effect of the B(MIDA) moiety. The transformation provided cis addition products using Cl+ or Br+ as the halogen source, while trans addition products were obtained when I+ was employed.

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