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

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Abstract

The synthesis of α-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.

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

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Article information


Submitted
28 Jan 2020
Accepted
10 Mar 2020
First published
10 Mar 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

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

Y. Zeng, X. Liu, D. Tan, W. Fan, Y. Li, Y. Guo and H. Wang, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC00722F

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