Synthesis and reactivity of Chiral N-Heterocyclic Iodanes
Date Issued
2021-09-20
Author(s)
Supervisors
Abstract
Hypervalent iodine compounds, in particular aryl-ʎ3-iodanes, have found widespread
applications for many organic transformations. Their reactivities are comparable to
highly oxidized period-6 metals, in particular Hg(II), Tl(III), and Pb(IV), with less
toxicity. All these merits make hypervalent iodine compounds suitable reagents to
perform a wide range of oxidative transformation reactions.
The first part of this thesis describes the efficient synthesis of novel triazole substituted
chiral hypervalent iodine catalysts. It also describes the reactivity and
selectivity of these new catalysts in different stereoselective oxidative transformations,
such as Kita-spirocyclizations, the α-tosyloxylation of propiophenone, oxidative
lactonizations, oxidative dearomtization of phenols and the oxidative rearrangement
of allyl alcohols.
The second part of the thesis describes the development of a novel enantioconvergent
benzylic hydroxylation by employing a chiral iodine catalyst that fulfills a dual purpose
as both oxidant and chiral ligand for a Cu co-oxidant.
Finally, the enantioselective cyclization of unsaturated amides using chiral aryl iodides
has been described, which has the facility to synthesize oxazoline derivatives. This
method can be used to prepare natural products and biologically active compounds
efficiently. Also, the asymmetric oxidative cyclization of naphthol compounds for the
synthesis of chiral spirooxazolines has been described. These compounds have many
applications in drugs and industrial applications.
applications for many organic transformations. Their reactivities are comparable to
highly oxidized period-6 metals, in particular Hg(II), Tl(III), and Pb(IV), with less
toxicity. All these merits make hypervalent iodine compounds suitable reagents to
perform a wide range of oxidative transformation reactions.
The first part of this thesis describes the efficient synthesis of novel triazole substituted
chiral hypervalent iodine catalysts. It also describes the reactivity and
selectivity of these new catalysts in different stereoselective oxidative transformations,
such as Kita-spirocyclizations, the α-tosyloxylation of propiophenone, oxidative
lactonizations, oxidative dearomtization of phenols and the oxidative rearrangement
of allyl alcohols.
The second part of the thesis describes the development of a novel enantioconvergent
benzylic hydroxylation by employing a chiral iodine catalyst that fulfills a dual purpose
as both oxidant and chiral ligand for a Cu co-oxidant.
Finally, the enantioselective cyclization of unsaturated amides using chiral aryl iodides
has been described, which has the facility to synthesize oxazoline derivatives. This
method can be used to prepare natural products and biologically active compounds
efficiently. Also, the asymmetric oxidative cyclization of naphthol compounds for the
synthesis of chiral spirooxazolines has been described. These compounds have many
applications in drugs and industrial applications.
Subjects
Organocatalysis
;
Chiral Hypervalentiodine
;
Enantioselective reactions
Institution
Type
Dissertation
Secondary publication
No
Language
English
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Name
PhD Thesis (Ayham Abazid)..pdf
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18.31 MB
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