Royal College of Surgeons in Ireland
Studies Concerning the Use of Activated Alkenes in Enantioselecti.pdf (7.44 MB)

Studies Concerning the Use of Activated Alkenes in Enantioselective Reactions.

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posted on 2019-11-22, 17:59 authored by Michela Scagnetti

Chapter 1:

A brief overview of the cinnamate esters equivalents and their behaviour under organocatalysis and metal catalysis.

Chapter 2.

The addition of bisulfite to olefins, discovered over a century ago, remains the most straightforward approach to aliphatic sulfonic acids. A catalytic enantioselective procedure has now been realized that employs a bifunctional aminothiourea catalyst. Sulfonic acids were obtained from chalcones in high yields and high enantioselectivity and in both configurations.

Chapter 3.

The use of 3-phenyl-5-vinyl-1,2,4-oxadiazole as activated alkene for the Morita-Baylis-Hillman reaction in presence of one equivalent of 1,8-Diazabicycloundec-7-ene gave good yields with several aldehydes bearing both aromatic and aliphatic substituent.

Chapter 4.

The asymmetric Michael addition of nitromethane to a series of 5-Vinyl-1,2,4-Oxadiazole promoted by cinchona alkaloids ammonium salts gave corresponding nitroadducts in medium-good yield but poor ee. Hydrolysis of nitroadduct, to unveil corresponding cinnamic acid, was performed successfully. This study can be extended to the addition of others nucleophiles to 5-Vinyl-1,2,4-Oxadiazole.

Chapter 5.

Diels-Alder reaction of dienophile 3-phenyl-5-vinyl-1,2,4-oxadiazole with several diene in presence of catalytic amount of Cu(OTf)2 gave good yield and excellent endo:exo ratio.



A thesis submitted for the degree of Doctor of Philosophy from the Royal College of Surgeons in Ireland in 2014.

Published Citation

Scagnetti M. Studies Concerning the Use of Activated Alkenes in Enantioselective Reactions [PhD Thesis]. Dublin: Royal College of Surgeons in Ireland; 2014.

Degree Name

  • Doctor of Philosophy (PhD)

Date of award


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