Open Accessα-Hydroxy boron-enabled regioselective access to bifunctional halo-boryl alicyclic ethers and α-halo borons
Author(s) -
Lucia Wang,
ShengJia Lin,
Yuemin Zhu,
Daniel Ferrante,
Timaf Ishak,
Yuki Baba,
Abhishek Sharma
Publication year - 2021
Publication title -
chemical communications
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.837
H-Index - 333
eISSN - 1364-548X
pISSN - 1359-7345
DOI - 10.1039/d1cc00336d
Subject(s) - regioselectivity , bifunctional , alicyclic compound , halo , chemistry , tetrahydrofuran , organic chemistry , catalysis , physics , quantum mechanics , solvent , galaxy
α-Hydroxy borons are an underutilized class of compounds and their only previous application involved oxidation into acylborons. Herein, we describe the synthesis of functionalized olefinic α-hydroxy borons and their utility to enable a novel and regioselective route to hitherto unknown bifunctional halo-boryl tetrahydrofurans/tetrahydropyrans and α-halo MIDA boronates. The orthogonally functionalized alicyclic ethers provided a building block-based approach for diversification of the tetrahydrofuran core.