Face selectivity in the borohydride reduction of 4-eq,6-ax-diaryl-5-azaadamantan-2-ones

Chemistry Letters

Volumn , Issue 8, 2000, Pages 956-957

  Jiménez Cruz, Federico ^a   Cetina, Raúl ^a   Ríos Olivares, Héctor ^a  

^a UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0034337695     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2000.956     Document Type: Article

References (15)

1. a) C. K. Cheung, L. T. Tseng, M.-H. Lin, S. Srivastava, and W. J. le Noble, J. Am. Chem. Soc., 108, 1598 (1986).
2. b) W. Adcock and N. A. Trout, J. Org. Chem., 56, 3229 (1991).
3. c) W. Adcock, J. Cotton, and N. A. Trout, J. Org. Chem., 59, 1867 (1994).
4. Y. Senda, M. Morita, and H. Itoh, J. Chem. Soc., Perkin Trans. 2, 1996, 221.
5. a) J. M. Hanh and W. J. le Noble, J. Am. Chem. Soc., 114, 1916 (1992),
6. b) J. Lau, E. M. Gonikberg, J. Hung, and W. J. le Noble, J. Am. Chem. Soc., 117, 11421 (1995).
7. A. S. Cieplak, J. Am. Chem. Soc., 103, 4540 (1981).
8. a) N. T. Ahn and O. Eisenstein, Nouv. J. Chim., 1, 61 (1977)
9. b) M. N. Paddon-Row, Y. D. Wu, and K. N. Houk, J. Am. Chem. Soc., 114, 10638 (1993).
10. B. W. Gung and M. A. Wolf, J. Org. Chem., 61, 232 (1996).
11. D. P. Becker and D. L. Flynn, Synthesis, 1992, 1080.
12. Typical Procedure for the Preparation of ketones 1: 0.746 mmol of the amino acetal 3 was dissolved in 5 mL of ethanol and 3 drops of 10% aqueous HCl. After refluxing for 20 minutes, an ethanolic solution of 4-substituted benzaldehyde (1.492 mmol) was added in hot, and the reflux continued by 24-72 h. Further treatment with 20% aqueous NaOH to pH = 8.5-9.0, the crude was extracted with chloroform (3 x 5 mL), then was dried over anhydrous sodium sulfate and evaporated in vacuo. After chromatographic purification, 4,6-diarylazaadamantanones were obtained and characterized.
13. C. Hansch, A. Leo, and R. W. Taft, Chem. Rev., 91, 165 (1991).
14. S. Tomoda and T. Senju, Tetrahedron, 55, 5303 (1999).
15. V. K. Yadav, G. Senthil, and D. A. Jerayaj, Tetrahedron, 55, 14211 (1999).