Abstract
Functionally substituted sulfones with stereogenic centers are valuable reagents in organic synthesis and key motifs in some bioactive compounds. The asymmetric Michael addition of β-ketosulfones to conjugated nitroalkenes in the presence of Ni(II) complexes with various chiral vicinal diamines was studied. This reaction provides convenient access to non-racemic 4-nitro-2-sulfonylbutan-1-ones with two stereocenters with high yield and excellent enantioselectivity (up to 99%). It has been established that the catalytic Michael reaction itself was carried out with high diastereoselectivity, but the Michael adducts may epimerize at the C-2 position at a significant rate. Conditions for the preparation of individual diastereomers were found.
Highlights
Sulfones are widely used in organic synthesis, in various reactions of C–C and C=C-bond formation [1,2,3,4]
It has been established that the catalytic Michael reaction itself was carried out with high diastereoselectivity, but the Michael adducts may epimerize at the C-2 position at a significant rate
For the catalytic activation of β-ketosulfones by metal complexes chiral Lewis acids may be considered as an alternative way to carry out the asymmetric Michael reaction with their participation
Summary
Sulfones are widely used in organic synthesis, in various reactions of C–C and C=C-bond formation [1,2,3,4]. The asymmetric Michael addition of β-ketosulfones to conjugated nitroalkenes in the presence of Ni(II) complexes with various chiral vicinal diamines was studied. There are only few examples of the use of sulfones as Michael donors in asymmetric addition reactions.
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