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Updated: Apr 20, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Asymmetric anti-selective Michael reaction of imidazole-modified ketones with trans-β-nitroalkenes
Dongxu Yang1, Linqing Wang, Dan Li
1School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, 510006 (P.R. China); Key Laboratory of Preclinical Study for New Drugs of Gansu Province, Lanzhou University, Lanzhou, 730000 (P.R. China).
Abstract:
The successful application of imidazole-modified ketones in asymmetric anti-selective Michael reactions with trans-β-nitroalkenes is presented by employing a newly developed 3-bromothiophene-modified chiral diamine ligand. The corresponding conjugate adduct was submitted to further transformations with Grignard reagents to solve the problem of α-site selectivity of simple linear ketones. Additionally, the syn-selective product was obtained by treating the anti-selective adduct with a simple base. In this way, the site-specific products for both diastereomers in the asymmetric conjugate addition of simple ketones to nitroalkenes can be obtained.
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