Asymmetric transfer hydrogenation of boronic acid pinacol ester (Bpin)-containing acetophenones. Issue 18 (19th April 2022)

• Record Type: Journal Article
• Authors: Zheng, Ye; Wills, Martin
• Is Part Of: Organic & biomolecular chemistry. Volume 20:Issue 18(2022)
• Page Start: 3742
• Page End: 3746
• Publication Date: 2022-04-19
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d2ob00569g
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : para - or meta -Bpin-containing acetophenone derivatives were reduced by asymmetric transfer hydrogenation (ATH), using Noyori–Ikariya catalysts, with formic acid/triethylamine, to alcohols in high enantiomeric excess. 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.