title: Asymmetric anti-selective Michael reaction of imidazole-modified ketones with trans-β-nitroalkenes.
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.
authors.affiliation: School 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).
authors.forename: Dongxu
authors.initials: D
authors.lastname: Yang
authors.forename: Linqing
authors.initials: L
authors.lastname: Wang
authors.forename: Dan
authors.initials: D
authors.lastname: Li
authors.forename: Fengxia
authors.initials: F
authors.lastname: Han
authors.forename: Depeng
authors.initials: D
authors.lastname: Zhao
authors.forename: Rui
authors.initials: R
authors.lastname: Wang
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D003959:Diamines / Q000737:chemistry*; D007093:Imidazoles / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D008024:Ligands; D009574:Nitro Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D003959:Diamines; D007093:Imidazoles; D007659:Ketones; D008024:Ligands; D009574:Nitro Compounds; C029899:imidazole
keywords: diamines; diastereoselectivity; ligand design; linear ketones; site selectivity