Synthesis of Benzomorphan Analogues by Intramolecular Buchwald–Hartwig Cyclization

@article{Khartulyari2007SynthesisOB,
  title={Synthesis of Benzomorphan Analogues by Intramolecular Buchwald–Hartwig Cyclization},
  author={Anton S. Khartulyari and Martin E. Maier},
  journal={European Journal of Organic Chemistry},
  year={2007},
  volume={2007},
  pages={317-324}
}
A new strategy toward the important class of benzomorphans is described. The key bond formation is based on an intramolecular Buchwald–Hartwig enolate arylation reaction. Thus, alkylation of piperidones with ortho-bromobenzyl bromides provides the necessary substrates. In the presence of a palladium catalyst, a sterically hindered phosphane ligand, and a base, carbon–carbon bond formation to tricyclic benzomorphan derivatives takes place. After removal of the N-protecting group, derivatization… 
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16 Citations

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References

SHOWING 1-10 OF 37 REFERENCES
Palladium-catalyzed intramolecular α-arylation of aliphatic ketone, formyl, and nitro groups
Nitrogen heterocycles by palladium-catalyzed cyclization of amino-tethered vinyl halides and ketone enolates.
The scope and limitations of Pd(0)-catalyzed intramolecular coupling of amino-tethered vinyl halides and ketone enolates as a methodology for the synthesis of nitrogen heterocycles have been studied.…
Rapid synthesis of the N-methylwelwitindolinone skeleton.
TLDR
An efficient, convergent synthesis of the core bicyclo-decane ring system of welwitindolinones is described and key steps include an intramolecular palladium-catalyzed enolate arylation reaction and a Curtius rearrangement to install the bridgehead isocyanate unit.
A new synthesis of 3-substituted-1H-indenes through reaction of o-(β-magnesioalkyl)phenylmagnesium dihalides with carboxylate esters
Palladium-Catalyzed Intramolecular a-Arylation of a-Amino Acid Esters
TLDR
The Pd-catalyzed intramolecular α-arylation of α-amino acid esters is described, and Reaction conditions have been found that allow the use of tert-butyl ester and N-(benzyloxycarbonyl) protecting groups.
Palladium-Catalyzed α-Arylation of Carbonyl Compounds and Nitriles
The palladium-catalyzed α-arylation of ketones has become a useful and general synthetic method. In this process, an enolate is generated from a ketone and base in the presence of an aryl halide, and…
Conversion of alkyl carbamates into amines via treatment with trimethylsilyl iodide
Reaction of the alkyl carbamates (1) with trimethylsilyl iodide (2) followed by methanolysis of the resulting trimethylsilyl carbamates (4), affords high yields of the corresponding amines (5), even…
Intramolecular Pd-mediated processes of amino-tethered aryl halides and ketones: insight into the ketone alpha-arylation and carbonyl-addition dichotomy. A new class of four-membered azapalladacycles.
TLDR
The dichotomy between ketone alpha-arylation and carbonyl-addition in the reactions of omega-(2-haloanilino) alkanones has been rationalized by the intermediacy of unprecedented four-membered azapalladacycles, from which X-ray data and chemical behavior are reported.
Improved catalysts for the palladium-catalyzed synthesis of oxindoles by amide alpha-arylation. Rate acceleration, use of aryl chloride substrates, and a new carbene ligand for asymmetric transformations.
TLDR
Mechanistic studies showed that the reaction involves rate-limiting oxidative addition of aryl halide, and use of new, optically active heterocyclic carbene ligands gave substantial enantioselectivity in formation of an alpha,alpha-disubstituted oxindole.
Palladium-Catalyzed α-Arylation of Esters and Amides under More Neutral Conditions
Two procedures for the α-arylation of carbonyl compounds under conditions that are more neutral than those of reactions of aryl halides with alkali metal enolates are reported. The first procedure…
...
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