Concise synthesis of the antidepressive drug candidate GSK1360707 by a highly enantioselective gold-catalyzed enyne cycloisomerization reaction.

@article{Teller2011ConciseSO,
  title={Concise synthesis of the antidepressive drug candidate GSK1360707 by a highly enantioselective gold-catalyzed enyne cycloisomerization reaction.},
  author={Henrik Teller and Alois F{\"u}rstner},
  journal={Chemistry},
  year={2011},
  volume={17 28},
  pages={
          7764-7
        }
}
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References

SHOWING 1-10 OF 40 REFERENCES
An enyne cycloisomerization approach to the triple reuptake inhibitor GSK1360707F.
The triple reuptake inhibitor GSK1360707F was synthesized via an efficient and scalable route that features an enyne cycloisomerization reaction catalyzed by either Pt(II) or Au(I). Key aspects of
Phosphoramidite gold(I)-catalyzed diastereo- and enantioselective synthesis of 3,4-substituted pyrrolidines.
TLDR
In this article the utility of phosphoramidite ligands in enantioselective Au(I) catalysis was explored in the development of highly diastereo- and enantiOSElective au(I)-catalyzed cycloadditions of allenenes in order to support the construction of three contiguous stereogenic centers.
6-(3,4-dichlorophenyl)-1-[(methyloxy)methyl]-3-azabicyclo[4.1.0]heptane: a new potent and selective triple reuptake inhibitor.
TLDR
In vivo microdialysis experiments in different animal models and receptor occupancy studies in rat confirmed that derivative 17 showed an appropriate profile to guarantee further progression of the compound.
Development of a New Synthesis for the Large-Scale Preparation of Triple Reuptake Inhibitor (−)-GSK1360707
The triple reuptake inhibitor, GSK1360707, was synthesized via an efficient, scalable route, which features a vinyl triflate Suzuki coupling followed by a single-step, double alkylative
Gold(I)-catalyzed enantioselective [4 + 2]-cycloaddition of allene-dienes.
An enantioselective gold(I)-catalyzed intramolecular [4 + 2]-cycloaddition of allenes and dienes is reported. The reactions allow for the asymmetric synthesis of trans-hexahydroindenes and
Mechanistic insights in gold-stabilized nonclassical carbocations: gold-catalyzed rearrangement of 3-cyclopropyl propargylic acetates.
The reaction of 3-cyclopropyl propargylic carboxylates with Au(I) and Au(III) catalysts affords selectively 5-(E)-alkylidenecyclopentenyl acetates via [3,3]-sigmatropic rearrangement of the
Phosphoramidites: privileged ligands in asymmetric catalysis.
TLDR
Recent developments in asymmetric catalysis with phosphoramidites used as ligands are discussed, with a focus on the formation of carbon-carbon and carbon-heteroatom bonds.
Unexpected inversions in asymmetric reactions: reactions with chiral metal complexes, chiral organocatalysts, and heterogeneous chiral catalysts.
The recognition of the optical activity of organic compounds, followed by the detailed analysis of optical isomerism,1 laid the foundation for the development of asymmetric syntheses, a group of
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