Palladium-Catalyzed Intramolecular Coupling of Aryl Halides and Ketone Enolates: Synthesis of Hexahydro-2,6-methano-1-benzazocines

Advanced Synthesis and Catalysis

Volumn 343, Issue 5, 2001, Pages 439-442

  Solé, Daniel ^a   Vallverdú, Lluís ^a   Bonjoch, Josep ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

Cyclization; Homogeneous catalysis; Nitrogen heterocycles; Palladium; Synthetic methods

Indexed keywords

EID: 0001467793     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/1615-4169(200107)343:5<439::AID-ADSC439>3.0.CO;2-G     Document Type: Article

References (30)

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14. Readily available from 1,4-cyclohexanedione monoethylene acetal by reductive animation with the corresponding 2-haloaniline, followed by benzylation or acylation, and acetal hydrolysis.
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19. 13C NMR, HR-MS, and/or microanalysis.
20. [1b].
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22. 3 as a ligand in Pd-catalyzed reactions, see: (a) A. F. Littke, G. C. Fu, Angew. Chem. Int. Ed. 1999, 38, 2411-2413; (b) T. Hundertmark, A. F. Littke, S. L. Buchwald, G. C. Fu, Org. Lett. 2000, 2, 1729-1731, and references cited therein.
23. 3 as a ligand in Pd-catalyzed reactions, see: (a) A. F. Littke, G. C. Fu, Angew. Chem. Int. Ed. 1999, 38, 2411-2413; (b) T. Hundertmark, A. F. Littke, S. L. Buchwald, G. C. Fu, Org. Lett. 2000, 2, 1729-1731, and references cited therein.
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25. 3 did not cause any reaction.
26. [2,4a,4c].
27. [4a].
28. Interestingly, in this work about δ-(2-haloaryl) ketones we have not observed processes of nucleophilic addition, recently reported in a series of β-and γ-(2-haloaryl) ketones: L. G. Quan, M. Lamrani, Y. Yamamoto, J. Am. Chem. Soc. 2000, 122, 4827-4828.
29. 2O, 60°C) in 43% yield, as an epimeric mixture (cis/trans ratio approximately 2:1).
30. Compound 11 was obtained as an epimeric mixture, cis/trans ratio approximately 2.2:1.