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Antoine Simonneau's thesis highlights the development of new
cycloisomerization reactions through the activation of alkynes with
gold complexes. First Simonneau describes 1,6-enynes and their
direct conversion into allenes through 1,5-hydride or ester
migration processes. The author and his team used appropriate
propargylic functional groups to achieve this conversion. This
study shows that O-tethered 1,6-enynes carrying a strained
cycloalkane at the propargylic position could undergo a
cyclopropanation/ring expansion cascade reaction. The author
employed this rearrangement as the starting point in the design of
a new macro cycle synthesis. The next part of the thesis focuses on
the cycloisomerization of diynes involving as the first step of the
process the rearrangement of one alkyne partner into an allene
thanks to a gold-catalyzed 1,3-shift of a propargylic ester. The
thesis discloses a new cycloisomerization pattern featuring a
1,5-carbonyl transfer, giving rise to unprecedented
cross-conjugated diketones. In the final part of the research,
Simmoneau investigates the gold-catalyzed cycloisomerization
mechanism of 1,6-enynes and questions the intermediacy of gold
acetylides. By the means of NMR and mass spectrometry analysis,
theoretical treatment and solution experiments, it was possible to
rule out the involvement of these species in the catalytic cycle.
This thesis has led to a number of publications in high-impact
journals.
Antoine Simonneau's thesis highlights the development of new
cycloisomerization reactions through the activation of alkynes with
gold complexes. First Simonneau describes 1,6-enynes and their
direct conversion into allenes through 1,5-hydride or ester
migration processes. The author and his team used appropriate
propargylic functional groups to achieve this conversion. This
study shows that O-tethered 1,6-enynes carrying a strained
cycloalkane at the propargylic position could undergo a
cyclopropanation/ring expansion cascade reaction. The author
employed this rearrangement as the starting point in the design of
a new macro cycle synthesis. The next part of the thesis focuses on
the cycloisomerization of diynes involving as the first step of the
process the rearrangement of one alkyne partner into an allene
thanks to a gold-catalyzed 1,3-shift of a propargylic ester. The
thesis discloses a new cycloisomerization pattern featuring a
1,5-carbonyl transfer, giving rise to unprecedented
cross-conjugated diketones. In the final part of the research,
Simmoneau investigates the gold-catalyzed cycloisomerization
mechanism of 1,6-enynes and questions the intermediacy of gold
acetylides. By the means of NMR and mass spectrometry analysis,
theoretical treatment and solution experiments, it was possible to
rule out the involvement of these species in the catalytic cycle.
This thesis has led to a number of publications in high-impact
journals.
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