Issue 31, 2020
From the journal:

Chemical Communications

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

Yao-Fu Zeng,*a   Xu-Ge Liu,b   Dong-Hang Tan,b   Wen-Xin Fan,b   Yi-Na Li,a   Yu Guo ORCID logo a  and  Honggen Wang ORCID logo *b  

* Corresponding authors

a Institute of Pharmacy and Pharmacology, Hunan Provincial Key Laboratory of Tumor Microenvironment Responsive Drug Research, University of South China, Hengyang, P. R. China

b School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, P. R. China
E-mail: wanghg3@mail.sysu.edu.cn

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

DOI
https://doi.org/10.1039/D0CC00722F
Article type
Communication
Submitted
28 Jan 2020
Accepted
10 Mar 2020
First published
10 Mar 2020

Chem. Commun., 2020,56, 4332-4335

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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, 56, 4332 DOI: 10.1039/D0CC00722F

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