N-Sulfinylpyrrolidine-containing ureas and thioureas as bifunctional organocatalysts.
Viera Poláčková,Dominika Krištofíková,Boglárka Némethová,Renáta Górová,Mária Mečiarová,Radovan Šebesta +5 more
TL;DR: In this article, the synthesis of bifunctional N-sulfinylureas and thioureas with an appended pyrrolidine unit is presented.
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Abstract: The synthesis of bifunctional N-sulfinylureas and thioureas with an appended pyrrolidine unit is presented. These organocatalysts were evaluated in Michael additions of aldehydes to nitroalkenes both under solvent-free conditions and in solution. The N-sulfinylurea catalyst was more efficient than the corresponding thiourea. For some substrates, enantioselectivities reached 98% ee. The stereogenic center on the sulfur did not have a considerable influence on the catalytic reactions. Under ball-milling conditions, the Michael adducts were obtained in good yields but with slightly lower enantiomeric purities than in solution. DFT calculations elucidated its mode of action and confirmed a dual activation mode, which combines enamine activation of aldehydes and hydrogen-bond activation of nitroalkenes.
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