Facial selectivity in the nucleophilic additions of vinylmagnesium bromide to bicyclo[2.2.2]oct-5-en-2-one derivatives

Journal of Organic Chemistry

Volumn 72, Issue 21, 2007, Pages 7992-8004

  Juo, Wan Jinq ^a   Lee, Tsung Ho ^a   Liu, Wen Cheng ^a   Ko, San ^a   Chittimalla, Santhosh Kumar ^a   Rao, Chitneni Prasad ^a   Liao, Chun Chen ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

DIASTEREOSELECTION; LEWIS ACIDS; NUCLEOPHILIC ADDITION; VINYLMAGNESIUM BROMIDE;

DERIVATIVES; ISOMERS; KETONES; LITHIUM COMPOUNDS; NUCLEOPHILES; VINYL RESINS;

STEREOSELECTIVITY;

ALUMINUM DERIVATIVE; BICYCLO COMPOUND; CESIUM CHLORIDE; CYCLOALKANE DERIVATIVE; KETONE DERIVATIVE; LEWIS ACID; LITHIUM BROMIDE; MAGNESIUM BROMIDE; MAGNESIUM DERIVATIVE; TITANIUM TETRACHLORIDE; UNCLASSIFIED DRUG; VINYL DERIVATIVE; VINYLMAGNESIUM BROMIDE; ZINC BROMIDE;

ADDITION REACTION; ANISOTROPY; ARTICLE; CATALYSIS; COPE REARRANGEMENT; DIASTEREOISOMER; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; REACTION ANALYSIS; ROOM TEMPERATURE; STEREOCHEMISTRY;

BICYCLO COMPOUNDS; CATALYSIS; KETONES; MAGNESIUM; MOLECULAR STRUCTURE; STEREOISOMERISM; VINYL COMPOUNDS;

EID: 35348823064     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo701401f     Document Type: Article

References (55)

1. Chu, C.-S.; Liao, C.-C.; Rao, P. D. J. Chem. Soc., Chem. Commun. 1996, 1537.
2. Uyehara, T.; Osanai, K.; Sugimoto, M.; Suzuki, I.; Yamamoto, M. J. Am. Chem. Soc. 1989, 111, 7264.
3. (a) Zimmerman, H. E.; Armesto, D. Chem. Rev. 1996, 96, 3065.
4. (b) Demuth, M. Org. Photochem. 1991, 11, 37.
5. (a) Givens, R. S.; Oettle, W. F.; Coffin, R. L.; Carlson, R. G. J. Am. Chem. Soc. 1971, 93, 3957.
6. (b) Demuth, M.; Schaffner, K. Angew. Chem., Int. Ed. Engl. 1982, 21, 820.
7. (c) Singh, V.; Porinchu, M. J. Chem. Soc., Chem. Commun. 1993, 134.
8. (a) Hsu, D.-S.; Rao, P. D.; Liao, C.-C. J. Chem. Soc., Chem. Commun. 1998, 1795.
9. (b) Singh, V.; Thomas, B. J. J. Org. Chem. 1997, 62, 5310.
10. (c) Hwang, J.-T.; Liao, C.-C. Tetrahedron Lett. 1991, 32, 6583.
11. (d) Demuth, M.; Hinsken, W. Angew. Chem., Int. Ed. 1985, 24, 973.
12. (e) Mehta, G.; Subrahmanyam, D. J. Chem. Soc., Perkin Trans. 1 1991, 395.
13. (a) Lee, T.-H.; Liao, C.-C.; Liu, W.-C. Tetrahedron Lett. 1996, 37, 5897.
14. (b) Hsu, P. -Y.; Lee, Y.-C.; Liao, C.-C. Tetrahedron Lett. 1998, 39, 659.
15. (a) Oplinger, J. A.; Paquette, L. A. Tetrahedron Lett. 1987, 28, 5441.
16. (b) Paquette, L. A.; Oplinger, J. A. Tetrahedron 1989, 45, 107.
17. Paquette, L. A.; Maleczka, R. E., Jr. J. Org. Chem. 1992, 57, 7118.
18. (a) Paquette, L. A.; Maleczka, R. E., Jr. J. Org. Chem. 1991, 56, 912.
19. (b) Maleczka, R. E., Jr.; Paquette, L. A. J. Org. Chem. 1991, 56, 6538.
20. Paquette, L. A. Tetrahedron 1997, 53, 13971.
21. Liu, W.-C.; Liao, C.-C. J. Chem. Soc., Chem. Commun. 1999, 117.
22. Banwell, M. G.; Dupuche, J. R. J. Chem. Soc., Chem. Commun. 1996, 869.
23. (a) Devaux, J.-F.; Hanna, I.; Lallemand, J. Y. J. Org. Chem. 1993, 58, 2349.
24. (b) Devaux, J.-F.; Fraisse, P.; Hanna, I.; Lallemand, J. Y. Tetrahedron Lett. 1995, 36, 9471.
25. (c) Berson, J. A.; Jones, M., Jr. J. Am. Chem. Soc. 1964, 86, 5019.
26. Chang, N.-C.; Day, H.-M.; Lu, W.-F. J. Org. Chem. 1989, 54, 4083.
27. Gao, S.-Y.; Ko, S.; Lin, Y.-L.; Peddinti, R. K.; Liao, C.-C. Tetrahedron 2001, 57, 297.
28. Chu, C.-S.; Lee, T.-H.; Rao, P. D.; Song, L.-D.; Liao, C.-C. J. Org. Chem. 1999, 64, 4111.
29. (a) Molander, G. A; Harris, C. R. J. Am. Chem. Soc. 1995, 117, 3705.
30. (b) Soderquist, J. A. Aldrichim. Acta 1991, 24, 15.
31. (c) Miranda Moreno, M. J. S.; Sa e Melo, M. L.; Campos Neves, A. S. Synlett 1994, 651.
32. (a) Cram, D. J.; Elhafez Fathy, A. A. J. Am. Chem. Soc. 1952, 74, 5828.
33. (b) For an excellent review on Cram's rule, including a review of chelation-controlled reactions, see: Mengel, A.; Reiser, O. Chem. Rev. 1999, 99, 1191.
34. (c) Reetz, M. T. Angew. Chem., Int. Ed. 1984, 23, 556.
35. (d) Reetz, M. T. Acc. Chem. Res. 1993, 26, 462.
36. Evans, D. A.; Allison, B. D.; Yang, M. G.; Masse, C. E. J. Am. Chem. Soc. 2001, 123, 10840 and references cited therein.
37. Otera, J. Modern Carbonyl Chemistry; Wiley-VCH: Weinheim, Germany, 2000.
38. (a) Luche, J. L. J. Am. Chem. Soc. 1978, 100, 2226.
39. (b) Gemal, A. L.; Luche, J. L. J. Am. Chem. Soc. 1981, 103, 5454.
40. (c) Marks, T. J.; Ernst, F. D. In Comprehensive Organometallic Chemistry; Wilkinson, G., Gordon, F., Stone, A., Abel, E. W., Eds.; Pergamon Press: Oxford, UK, 1982; Vol. 3, p 173.
41. (d) Imamoto, T.; Sugiura, Y.; Takiyama, N. Tetrahedron Lett. 1984, 25, 4233.
42. (e) Imamoto, T.; Takiyama, N.; Nakamura, K. Tetrahedron Lett. 1985, 26, 4763.
43. (f) Imamoto, T. Pure Appl. Chem. 1990, 62, 747.
44. (g) Reetz, M. T. Pure Appl. Chem. 1992, 64, 351.
45. (h) Liu, H.-J.; Shia, K.-S.; Shang, X.; Zhu, B.-Y. Tetrahedron 1999, 55, 3803.
46. (i) Gracza, T.; Szolcsanyi, P. Molecules 2000, 5, 1386.
47. (j) Uttaro, J.-P.; Audran, G.; Galano, J.-M.; Monti, H. Tetrahedron Lett. 2002, 43, 2757.
48. (k) Matsukawa, S.; Funabashi, Y.; Imamoto, T. Tetrahedron Lett. 2003, 44, 1007.
49. (l) Iwamoto, M.; Miyano, M.; Utsugi, M.; Kawada, H.; Nakada, M. Tetrahedron Lett. 2004, 45, 8647.
50. Pudzianowski, A. T.; Barrish, J. C.; Spergel, S. H. Tetrahedron Lett. 1992, 33, 293.
51. (a) Mehta, G.; Khan, F. A.; Ganguly, B.; Chandrasekhar, J. J. Chem. Soc., Chem. Commun. 1992, 1711.
52. (b) Mehta, G.; Khan, F. A. J. Am. Chem. Soc. 1990, 112, 6140.
53. Deva Priyakumar, U. D.; Shastri, G. N.; Mehta, G. Tetrahedron 2004, 60, 3465.
54. Berson, J. A.; Jones, M., Jr. J. Am. Chem. Soc. 1964, 86, 5019.
55. Still, W. C.; Schneider, J. A. Tetrahedron Lett. 1980, 21, 1035.