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  • Title: Asymmetric anti-selective Michael reaction of imidazole-modified ketones with trans-β-nitroalkenes.
    Author: Yang D, Wang L, Li D, Han F, Zhao D, Wang R.
    Journal: Chemistry; 2015 Jan 19; 21(4):1458-62. PubMed ID: 25446668.
    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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