B α-Hydroxy boron-enabled regioselective access to bifunctional halo-boryl alicyclic ethers and α-halo borons

Lucia Wang; Shengjia Lin; Yawei Zhu; Daniel Ferrante; Timaf Ishak; Yuki Baba; Abhishek Sharma

doi:10.1039/d1cc00336d

B α-Hydroxy boron-enabled regioselective access to bifunctional halo-boryl alicyclic ethers and α-halo borons

Lucia Wang, Shengjia Lin, Yawei Zhu, Daniel Ferrante, Timaf Ishak, Yuki Baba, Abhishek Sharma

Department of Chemistry and Chemical Biology

Research output: Contribution to journal › Article › peer-review

3 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	4564-4567
Number of pages	4
Journal	Chemical Communications
Volume	57
Issue number	37
DOIs	https://doi.org/10.1039/d1cc00336d
State	Published - 7 May 2021

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abstract = "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.",

author = "Lucia Wang and Shengjia Lin and Yawei Zhu and Daniel Ferrante and Timaf Ishak and Yuki Baba and Abhishek Sharma",

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T1 - B α-Hydroxy boron-enabled regioselective access to bifunctional halo-boryl alicyclic ethers and α-halo borons

AU - Wang, Lucia

AU - Lin, Shengjia

AU - Zhu, Yawei

AU - Ferrante, Daniel

AU - Ishak, Timaf

AU - Baba, Yuki

AU - Sharma, Abhishek

N1 - Publisher Copyright: © The Royal Society of Chemistry.

PY - 2021/5/7

Y1 - 2021/5/7

N2 - 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.

AB - 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.

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AN - SCOPUS:85105374574

SN - 1359-7345

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JO - Chemical Communications

JF - Chemical Communications

IS - 37

ER -

B α-Hydroxy boron-enabled regioselective access to bifunctional halo-boryl alicyclic ethers and α-halo borons

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