New exo/endo selectivity observed in monohydrolysis of dialkyl bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylates

Tetrahedron Letters

Volumn 44, Issue 47, 2003, Pages 8567-8570

  Niwayama, Satomi ^a   Hiraga, Yoshikazu ^a  

^a OKLAHOMA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; NORBORNENE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; HYDROLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0142138296     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.09.131     Document Type: Article

References (20)

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11. For example, see: (a) Gleiter, R.; Paquette, L. A. Acc. Chem. Res. 1983, 16, 328-334; (b) Kobuke, Y.; Sugimoto, T.; Furukawa, J. J. Org. Chem. 1976, 41, 1457-1459; (c) Brown, F. K.; Houk, K. N. J. Am. Chem. Soc. 1984, 107, 1971-1978.
12. For example, see: (a) Gleiter, R.; Paquette, L. A. Acc. Chem. Res. 1983, 16, 328-334; (b) Kobuke, Y.; Sugimoto, T.; Furukawa, J. J. Org. Chem. 1976, 41, 1457-1459; (c) Brown, F. K.; Houk, K. N. J. Am. Chem. Soc. 1984, 107, 1971-1978.
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15. 4: 210.0892, found 210.0892.
16. Formation of a small amount of dicarboxylic acids was occasionally observed due to this prolonged reaction time.
17. Niwayama S. Tetrahedron Lett. 41:2000;10163-10166.
18. The somewhat smaller difference in the yields for monohydrolyses of 1b and 2b than those of 1a and 2a may be attributed to the differences in their solubilities in this reaction mixture.
19. 4: 210.0892, found 210.0892.
20. Clapham G., Shipman M. Tetrahedron. 56:2000;1127-1134.