Synthesis of the kappa-agonist CJ-15,161 via a palladium-catalyzed cross-coupling reaction.

@article{Ghosh2002SynthesisOT,
  title={Synthesis of the kappa-agonist CJ-15,161 via a palladium-catalyzed cross-coupling reaction.},
  author={Arun K. Ghosh and Janice E. Sieser and St{\'e}phane Caron and Timothy J. N. Watson},
  journal={Chemical communications},
  year={2002},
  volume={15},
  pages={
          1644-5
        }
}
Syntheses of CJ-15,161 (1) involving intermolecular N-arylation of an appropriately functionalized diamine, obtained from the precursor alpha-amino acids or, more conveniently, from the corresponding 1,2-amino alcohols via 1,2,3-oxathiazolidine-2,2-dioxide 22, are reported. 
11 Citations

Topics from this paper

Efficient synthesis of the κ-opioid receptor agonist CJ-15,161: four stereospecific inversions at a single aziridinium stereogenic center
Abstract An efficient four-step sequence has been developed for the synthesis of the κ-opioid receptor agonist CJ-15,161. The process features four consecutive regioselective and stereospecific
Chemoselectivity control in the reactions of 1,2-cyclic sulfamidates with amines.
TLDR
It is found that DMF and DMSO behave not only as polar aprotic solvents but also as O-nucleophilic reagents, allowing the incorporation of an oxygen atom at a quaternary center of the electrophile, with inversion of configuration.
Biaryl phosphane ligands in palladium-catalyzed amination.
TLDR
The application ofadium-catalyzed amination reactions of aryl halides in C-N cross-coupling reactions in the synthesis of heterocycles and pharmaceuticals, in materials science, and in natural product synthesis is discussed.
Diastereoselective Synthesis and Configurational Assignment of Novel Functionalized Cyclic Sulfamidites Precursors of Cyclic Sulfamidates
New 3,4,5-trisubstituted sulfamidites were prepared through cyclization of β-amino alcohol diesters with thionyl chloride. The oxidation of these N-alkylated sulfamidites into the corresponding
Chiral Lithium N,P-amide Complexes. Synthesis, Applications and Structural Studies by NMR and DFT.
Enantiospecific synthesis reactions are of intense interest, owing to the increasing request for enantiopure compounds in both research and industry. Lithium amides containing a secondary chelating
2‐(Di‐tert‐butylphosphino)biphenyl
[224311-51-7] C20H27P (MW 298.41) InChI = 1/C20H27P/c1-19(2,3)21(20(4,5)6)18-15-11-10-14-17(18)16-12-8-7-9-13-16/h7-15H,1-6H3 InChIKey = CNXMDTWQWLGCPE-UHFFFAOYAH
Substituent Effects on the Reactivity of Cyclic Tertiary Sulfamidates.
TLDR
It is demonstrated both experimentally and computationally that a proper selection of the substitution scheme can enhance the synthetic scope of α-methylisoserine-derived sulfamidates, switching off and on the nucleophilic ring-opening in a controlled manner.
Aryl C(sp2)–X Coupling (X = C, N, O, Cl) and Facile Control of N-Mono- and N,N-Diarylation of Primary Alkylamines at a Pt(IV) Center
TLDR
The first example of an unprecedented and fast C(sp2)–X reductive elimination from a series of isolated Pt(IV) aryl complexes is presented and applied in unprecedented mono- and di-N-arylation of amino acid derivatives (lysine and tryptophan) under very mild conditions.
Biarylphosphanliganden in der palladiumkatalysierten Aminierung
In den vergangenen 12 Jahren erfuhr die palladiumkatalysierte Aminierung von Arylhalogeniden eine rasche Entwicklung, die durch die Einfuhrung neuer Ligandenklassen vorangetrieben wurde.
...
1
2
...

References

SHOWING 1-10 OF 16 REFERENCES
Efficient hydrolysis of β-aminosulfamic acids using a Lewis acid and a thiol for the synthesis of 2,3-diaminopropanoate derivatives
Abstract New hydrolysis conditions for β-aminosulfamic acids produced from the opening of a cyclic sulfamidate with a variety of primary or secondary amines have been developed. This new hydrolysis
Solid phase synthesis of aryl amines via palladium catalyzed amination of resin-bound aromatic bromides
Abstract Polymer-bound aromatic bromides were found to readily undergo Pd-catalyzed amination with a number of primary and secondary alkyl- and arylamines to give, after cleavage from the support, a
Transition Metal Catalyzed Synthesis of Arylamines and Aryl Ethers from Aryl Halides and Triflates: Scope and Mechanism.
  • J. Hartwig
  • Chemistry, Medicine
    Angewandte Chemie
  • 1998
Oxidative addition and reductive elimination are the central steps in new palladium-catalyzed chemistry that forms C-N and C-O bonds in arylamines and ethers. In the potential mechanism shown on the
The preparation of β-substituted amines from mixtures of epoxide opening products via a common aziridinium ion intermediate
Abstract Here we describe a one-pot synthesis of a series of β-substituted amines as single enantiomers from an initial regioisomeric mixture of styrene oxide ring-opening products. We also report
Stereo- and regiochemical aspects of the Mitsunobu reaction in synthesis of chiral amino ether ligands for asymmetric reactions
Abstract Combination of the neighboring amino group participating Mitsunobu reaction and cyclic sulphamidate procedure provided efficient stereo- and regioselective synthesis of chiral amino ether
The first general method for palladium-catalyzed Negishi cross-coupling of aryl and vinyl chlorides: use of commercially available Pd(P(t-Bu)(3))(2) as a catalyst.
  • C. Dai, G. C. Fu
  • Chemistry, Medicine
    Journal of the American Chemical Society
  • 2001
TLDR
With a single protocol, commercially available Pd(P(t-Bu)(3))(2) can effect the Negishi cross-coupling of a wide range of aryl and vinyl chlorides with aryal- and alkylzinc reagents, and it efficiently generates sterically hindered biaryls.
Room-Temperature Palladium-Catalyzed Amination of Aryl Bromides and Chlorides and Extended Scope of Aromatic C-N Bond Formation with a Commercial Ligand.
The reactions of aryl bromides with amines occurs at room temperature when using Pd(0) and P(t-Bu)(3) in a 1:1 ratio, and the reactions of aryl chlorides occur at room temperature or 70 degrees C.
Scope and limitations of the Pd/BINAP-catalyzed amination of aryl bromides.
TLDR
Mixtures of Pd(2)(dba)(3) or PD(OAc)(2) and BINAP catalyze the cross-coupling of amines with a variety of aryl bromides, and certain classes of secondary amines are also effectively transformed.
Palladium-catalyzed amination of aryl halides and sulfonates
Abstract In this review, the progress made in the palladium-catalyzed amination of aryl halides and sulfonates is described with particular attention given to applications in synthetic organic
Solid phase synthesis of aryl amines
Abstract A method for the solid phase synthesis of aryl amines is reported. The method involves a palladium mediated coupling reaction between aryl bromides and amines. The products are isolated in
...
1
2
...