Gold-catalyzed assembly of heterobicyclic systems

Journal of the American Chemical Society

Volumn 127, Issue 19, 2005, Pages 6962-6963

  Zhang, Liming ^a   Kozmin, Sergey A ^a  

^a UNIVERSITY OF CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GOLD;

ARTICLE; CATALYSIS; CHEMICAL BOND; CYCLIZATION; INFRARED RADIATION; ISOMERIZATION; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 18744401616     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja051110e     Document Type: Article

References (29)

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12. (i) Yao, X.; Li, C. J. Am. Chem. Soc. 2004, 126, 6884.
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17. (n) Sherry, B. D.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 15978.
18. For selected examples of gold-based alkene activation, see: (a) He, C.; Shi, Z. J. Am. Chem. Soc. 2004, 126, 5964.
19. (b) Yao, X.; Li, C. J. Am. Chem. Soc. 2004, 126, 6884.
20. Zhang, L.; Kozmin, S. A. J. Am. Chem. Soc. 2004, 126, 11806.
21. 3-catalyzed 6-exo-dig cyclizations of 1,6-enynes, followed by alcohol trapping, see: Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echevarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511; also see ref 2e.
22. 4, see: Imamura, K.; Yoshikawa, E.; Gevorgyan, V.; Yamamoto, Y. J. Am. Chem. Soc. 1998, 120, 5339.
23. For a single example of Au-catalyzed 6-endo-dig cyclization, followed by methanol trapping, see ref 21.
24. For an example of Brønsted acid-promoted alkyne activation, see: Zhang, L.; Kozmin, S. A. J. Am. Chem. Soc. 2004, 126, 10204.
25. For gold-catalyzed alkyne animation with primary amines, see: Fukuda, Y.; Utimoto, K.; Nozaki, H. Heterocycles 1987, 25, 297.
26. Semiempirical calculations revealed that trans-oxabicyclo[4.3.0]nonene 19 was 7.7 kcal/mol higher in energy compared to the corresponding cis-fused bicyclic ether.
27. Bicyclic ether 19 was produced as a 9:1 mixture of trans:cis diastereomers corresponding to the 9:1 mixture E:Z geometrical isomers of alkene 18.
28. 3 (10 mol %) afforded a 2:1 mixture of trans:cis-fused bicyclic ethers 19, which were separated and fully characterized. See Supporting Information for details.
29. The structure of 25 was verified by X-ray crystallography. See Supporting Information for details.