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Asymmetric transfer hydrogenation of boronic acid pinacol ester (Bpin)-containing acetophenones
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Zheng, Ye and Wills, Martin (2022) Asymmetric transfer hydrogenation of boronic acid pinacol ester (Bpin)-containing acetophenones. Organic & Biomolecular Chemistry, 20 (18). pp. 3742-3746. doi:10.1039/d2ob00569g ISSN 1477-0520.
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WRAP-Asymmetric-transfer-hydrogenation-boronic-acid-pinacol-ester-acetophenones-2022.pdf - Published Version - Requires a PDF viewer. Available under License Creative Commons Attribution. Download (557Kb) | Preview |
Official URL: https://doi.org/10.1039/d2ob00569g
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.
Item Type: | Journal Article | ||||||||
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Subjects: | Q Science > QD Chemistry | ||||||||
Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | ||||||||
SWORD Depositor: | Library Publications Router | ||||||||
Library of Congress Subject Headings (LCSH): | Bioinorganic chemistry, Chemistry, Organic, Hydrogenation, Ketones | ||||||||
Journal or Publication Title: | Organic & Biomolecular Chemistry | ||||||||
Publisher: | Royal Society of Chemistry | ||||||||
ISSN: | 1477-0520 | ||||||||
Official Date: | 14 May 2022 | ||||||||
Dates: |
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Volume: | 20 | ||||||||
Number: | 18 | ||||||||
Page Range: | pp. 3742-3746 | ||||||||
DOI: | 10.1039/d2ob00569g | ||||||||
Status: | Peer Reviewed | ||||||||
Publication Status: | Published | ||||||||
Access rights to Published version: | Open Access (Creative Commons) | ||||||||
Date of first compliant deposit: | 3 May 2022 | ||||||||
Date of first compliant Open Access: | 4 May 2022 | ||||||||
RIOXX Funder/Project Grant: |
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