Issue 18, 2022

Asymmetric transfer hydrogenation of boronic acid pinacol ester (Bpin)-containing acetophenones

Abstract

A series of Bpin-containing acetophenone derivatives were reduced by asymmetric transfer hydrogenation (ATH), using Noyori–Ikariya catalysts, with formic acid/triethylamine, to alcohols in high ee when the Bpin is in the para- or meta-position. Substrates containing ortho-Bpin groups were reduced in lower ee, with formation of a cyclic boron-containing group. The products were converted to substituted derivatives using Pd-catalysed coupling reactions. The results represent the first examples of ATH of Bpin-containing ketones.

Graphical abstract: Asymmetric transfer hydrogenation of boronic acid pinacol ester (Bpin)-containing acetophenones

Supplementary files

Article information

Article type
Paper
Submitted
25 Mar 2022
Accepted
12 Apr 2022
First published
12 Apr 2022
This article is Open Access
Creative Commons BY license

Org. Biomol. Chem., 2022,20, 3742-3746

Asymmetric transfer hydrogenation of boronic acid pinacol ester (Bpin)-containing acetophenones

Y. Zheng and M. Wills, Org. Biomol. Chem., 2022, 20, 3742 DOI: 10.1039/D2OB00569G

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