Remote Exo/Endo selectivity in selective monohydrolysis of dialkyl bicyclo[2.2.1]heptane-2,3-dicarboxylate derivatives

Journal of Organic Chemistry

Volumn 75, Issue 11, 2010, Pages 3775-3780

  Niwayama, Satomi ^a   Cho, Hanjoung ^a   Zabet Moghaddam, Masoud ^a   Whittlesey, Bruce R ^a  

^a TEXAS TECH UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COSOLVENTS; DIESTERS; ESTER GROUPS; FACIAL SELECTIVITY; MONOHYDROLYSIS; NORBORNANE; NORBORNENES; REACTION CENTER;

CARBOXYLATION; ESTERS;

ESTERIFICATION;

CARBOXYLIC ACID DERIVATIVE; ENDO 3 ETHOXYCARBONYL ENDO,ENDO 5,6 DIMETHYLBICYCLO[2.2.1]HEPTANE EXO 2 CARBOXYLIC ACID; ENDO 3 ETHOXYCARBONYL EXO,EXO 5,6 ISOPROPYLIDENEDIOXYBICYCLO[2.2.1]HEPTANE EXO 2 CARBOXYLIC ACID; ENDO 3 ETHOXYCARBONYLBICYCLO[2.2.1]HEPT 2 ENE 2 EXO CARBOXYLIC ACID; ENDO 3 ETHOXYCARBONYLBICYCLO[2.2.1]HEPTANE 2 EXO CARBOXYLIC ACID; ENDO 3 METHOXYCARBONYL ENDO,ENDO 5,6 DIMETHYLBICYCLO[2.2.1]HEPTANE EXO 2 CARBOXYLIC ACID; ENDO 3 METHOXYCARBONYL EXO,EXO 5,6 ISOPROPYLIDENEDIOXYBICYCLO[2.2.1]HEPTANE EXO 2 CARBOXYLIC ACID; ENDO 3 METHOXYCARBONYLBICYCLO[2.2.1]HEPT 2 ENE 2 EXO CARBOXYLIC ACID; ENDO 3 METHOXYCARBONYLBICYCLO[2.2.1]HEPTANE 2 EXO CARBOXYLIC ACID; EXO 3 ETHOXYCARBONYL EXO,EXO 5,6 ISOPROPYLIDENEDIOXYBICYCLO[2.2.1]HEPTANE ENDO 2 CARBOXYLIC ACID; EXO 3 ETHOXYCARBONYLBICYCLO[2.2.1]HEPT 2 ENE ENDO 2 CARBOXYLIC ACID; EXO 3 ETHOXYCARBONYLBICYCLO[2.2.1]HEPTANE 2 ENDO CARBOXYLIC ACID; EXO 3 METHOXYCARBONYL EXO,EXO 5,6 ISOPROPYLIDENEDIOXYBICYCLO[2.2.1]HEPTANE ENDO 2 CARBOXYLIC ACID; EXO 3 METHOXYCARBONYLBICYCLO[2.2.1]HEPT 2 ENE ENDO 2 CARBOXYLIC ACID; EXO 3 METHOXYCARBONYLBICYCLO[2.2.1]HEPTANE 2 ENDO CARBOXYLIC ACID; NORBORNANE DERIVATIVE; NORBORNENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; COVALENT BOND; HYDROLYSIS;

CARBOXYLIC ACIDS; HEPTANES; HYDROLYSIS; NORBORNANES; SOLVENTS;

EID: 77952963392     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100564e     Document Type: Article

References (34)

1. Brown, H. C.; Kawakami, J. H. J. Am. Chem. Soc. 1970, 92, 1990-1995
2. Brown, H. C.; Hammar, W. J.; Kawakami, J. H.; Rothberg, I.; Vander Jugt, D. L. J. Am. Chem. Soc. 1967, 104, 6381-6382
3. Brown, H. C.; Kawakami, J. H.; Liu, K.-T. J. Am. Chem. Soc. 1973, 95, 2209-2216
4. Schleyer, P. v. R. J. Am. Chem. Soc. 1967, 89, 701-703
5. Rondan, N. G.; Paddon-Row, M. N.; Caramella, P.; Houk, K. N. J. Am. Chem. Soc. 1981, 103, 2436-2438
6. Rondan, N. G.; Paddon-Row, M. N.; Caramella, P.; Mareda, J.; Mueller, P. H.; Houk, K. N. J. Am. Chem. Soc. 1982, 104, 4974-4976
7. Inagaki, S.; Fujimoto, H.; Fukui, K. J. Am. Chem. Soc. 1976, 98, 4054-4061
8. Sugimoto, T.; Kobuke, Y.; Furukawa, J. J. Org. Chem. 1976, 41, 1457-1459
9. Paquette, L. A.; Kravetz, T. M.; Boehm, M. C.; Gleiter, R. J. Org. Chem. 1983, 48, 1250-1257
10. Subramanyam, R.; Bartlett, P. D.; Iglesias, G. Y. M.; Watson, W. H.; Galloy, J. J. Org. Chem. 1982, 47, 4491-4498
11. Avenati, M.; Vogel, P. Helv. Chim. Acta 1983, 66, 1279-1287
12. Brown, F. K.; Houk, K. N. J. Am. Chem. Soc. 1985, 107, 1971-1978
13. Klunder, A. J. H.; van Gastel, F. J. C.; Zwanenburg, B. Tetrahedron Lett. 1988, 29, 2697-2700
14. Van der Eycken, J.; Vandewalle, M.; Heinemann, G.; Laumen, K.; Schneider, M. P; Kredel, J.; Sauer, J. J. Chem. Soc., Chem. Commun. 1989, 306-308
15. Van Gastel, F. J. C.; Klunder, A. J. H.; Zwanenburg, B. Recl. Trav. Chim. Pays-Bas 1991, 110, 175-184
16. Niwayama, S.; Hiraga, Y. Tetrahedron Lett. 2003, 44, 8567-8570
17. Niwayama, S. J. Org. Chem. 2000, 65, 5834-5836
18. Niwayama, S. J. Synth. Org. Chem., Jpn. 2008, 66, 983-994
19. Niwayama, S.; Wang, H.; Hiraga, Y.; Clayton, J. C. Tetrahedron Lett. 2007, 48, 8508-8510
20. Niwayama, S.; Rimkus, A. Bull. Chem. Soc. Jpn. 2005, 78, 498-500
21. Cho, H.; Niwayama, S. 238th American Chemical Society National Meeting, Washington, DC, August 2009, ORGN 516
22. Niwayama, S.; Cho, H.; Lin, C. Tetrahedron Lett. 2008, 49, 4434-4436
23. Niwayama, S.; Cho, H. Chem. Pharm. Bull. 2009, 57, 508-510
24. Lauria, F.; Vecchietti, V.; Logemann, W.; Tosolini, G.; Dradi, E. Tetrahedron 1969, 25, 3989-3998
25. Brown, H. C.; Muzzio, J. J. Am. Chem. Soc. 1966, 88, 2811-2822
26. Moreno-Vargas, A. J.; Schutz, C.; Scopelliti, R.; Vogel, P. J. Org. Chem. 2003, 68, 5632-5640
27. Maruyama, K.; Tamiaki, H. J. Org. Chem. 1986, 51, 602-606
28. Kikkawa, S.; Nomura, M.; Uno, Y.; Matsubara, M.; Yanagida, Y. Bull. Chem. Soc. Jpn. 1972, 45, 2523-2527
29. Yanagida, Y.; Shigesato, H.; Nomura, M.; Kikkawa, S. Bull. Chem. Soc. Jpn. 1974, 47, 677-680
30. Yanagida, Y.; Shigesato, H.; Nomura, M.; Kikkawa, S. Nihon Kagaku Kaishi 1975, 4, 657-660
31. Yanagida, Y.; Yokota, T.; Nomura, M.; Kikkawa, S. Nihon Kagaku Kaishi 1975, 4, 652-656
32. For example, see: Nishihara, Y.; Inoue, Y.; Nakayama, Y.; Shiono, T.; Takagi, K. Macromolecules 2006, 39, 7458-7460
33. Delaude, L.; Demonceau, A.; Noels, A. F. Macromolecules 2003, 36, 1446-1456
34. Pollino, J. M.; Stubbs, L. P.; Weck, M. Macromolecules 2003, 36, 2230-2234