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Aromatic and sterically hindered amines in aza-Michael reaction : solvent and high pressure effects

Abstract : Along this PhD work, we have reported that the unique combination of hexafluoroisopropanol (HFIP), employed as solvent, and hyperbaric conditions (10-15 kbar) allows unprecedented 1,4-addition of poor nucleophiles such as aromatic amines onto sluggish (cumbersome) Michael acceptors without any promoter nor work-up. Moreover, The hetero-Michael addition of functionally substituted anilines to α,β-unsaturated esters is significantly defined by the difference of acidity between the solvent and the amine. Reaction with more basic anilines proceeds smoothly in methanol. In contrast, very polar protic solvent such as fluorinated alcohols (HFIP and TFE) favor the aza-Michael addition of more weak nucleophiles. Finally, green and catalyst-free method of new amino acid derivatives construction containing adamantane and aziridine fragments was developed. And it is proved that aza-Michael reaction initiates the formation of heterocycle.
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https://tel.archives-ouvertes.fr/tel-01940116
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Submitted on : Friday, November 30, 2018 - 8:53:11 AM
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Alena Fedotova. Aromatic and sterically hindered amines in aza-Michael reaction : solvent and high pressure effects. Organic chemistry. Normandie Université; Rossijskaâ akademiâ nauk. Sibirskoe otdelenie, 2018. English. ⟨NNT : 2018NORMR056⟩. ⟨tel-01940116⟩

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