Stereoselective Synthesis of Enantiopure Abasic Nucleosides and 4-Nitroisoxazoles
A brief overview on organocatalysis and its application in 1,4-Michael type reactions.
We have described a 1,6-Michael type addition of 4-pyridilacetonitrile to 4-nitro-5-styril-isoxazoles under PTC and bifunctional catalysis.
We have reported a organocatalytic 1,4-conjugate addition of 1,3-dicarbonyl compounds (i.e. acetylacetone and malonate esters) to 4-nitro-5-styril-isoxazoles under bifunctional catalysis conditions.
Herein we report organocatalytic aza-Michael additions to 4-nitro-5-styril-isoxazoles of different N-nucleophiles (i.e. indoline, 1H-benzotriazole and O-benzylhydroxylamine) as Michael donors for the generation of building blocks with high potential synthetic utility.
An enantioselective Michael-type conjugate addition of boronic acids, catalysed by chiral transition metal complexes, effective in the formation of C-C bonds, has been described using 4-nitro-5-styril-isoxazoles as Michael acceptors.
The development of novel C-nucleosides analogues bearing functional groups able to complex divalent metal ions has been investigated. Here we describe the preparation of modified nucleosides, prepared from a cheap and readily available starting material (i.e. 2-deoxyribose).
First SupervisorProfessor Mauro F. A. Adamo
CommentsA thesis submitted for the degree of Doctor of Philosophy from the Royal College of Surgeons in Ireland in 2016.
Published CitationTorri F. Stereoselective Synthesis of Enantiopure Abasic Nucleosides and 4-Nitroisoxazoles [PhD Thesis]. Dublin: Royal College of Surgeons in Ireland; 2016.
- Doctor of Philosophy (PhD)