New reduction reaction of benzylic alcohols with acid and proof of the intermolecular hydride shift mechanism

Heterocycles

Volumn 53, Issue 2, 2000, Pages 359-372

  Kihara, Masaru ^a   Andoh, Jun Ichi ^a   Yoshida, Chiaki ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; ALKANE DERIVATIVE; DEUTERIUM; HYDROXYL GROUP; ISOQUINOLINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; MOLECULAR DYNAMICS; REDUCTION; STEREOCHEMISTRY;

EID: 0034142047     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-99-8786     Document Type: Article

References (23)

1. a) G. S. Hamilton, R. E. Mewshaw, C. M. Bryant, Y. Feng, G. Endemann, K. S. Madden, J. E. Janczak, J. Perumattam, L. W. Stanton, X. Yang, Z. Yin, B. Venkataramen, and D. Y. Liu, J. Med. Chem., 1995, 38, 1650;
2. b) A. D. Gribble, R. J. Ife., A. Shaw, D. McNair, C. E. Novelli, S. Bakewell, V. P. Shah, R. E. Dolle, P. H. Groot, N. Pearce, J. Yates, D. Tew, H. Boyd, S. Ashman, D. S. Eggleston, R. C. Haltiwanger, and G. Okafo, J. Med. Chem., 1998, 41, 3582.
3. G. R. Martinez, K. A. M. Walker, D. R. Hirschfeld, J. J. Bruno, D. S. Yang, and P. J. Maloney, J. Med. Chem., 1992, 35, 620.
4. C. M. Tegley, L. Zhi, K. B. Marschke, M. M. Gottardis, Q. Yang, and T. K. Jones, J. Med. Chem., 1998, 41, 4354.
5. M. Kihara, M. Ikeuchi, and Y. Nagao, Drug Design and Discovery, 1995, 12, 259.
6. a) M. Kihara, M. Kashimoto, Y. Kobayashi, and S. Kobayashi, Tetrahedron Lett., 1990, 31, 5347;
7. b) M. Kihara, M. Kashimoto, and Y. Kobayashi, Tetrahedron, 1992, 48, 67;
8. c) M. Kihara, M. Kashimoto, Y. Kobayashi, Y. Nagao, and H. Moritoki, Chem.Pharm.Bull, 1994, 42, 67.
9. M. Kihara, J. Andoh, and C. Yoshida, Heterocycles, 1998, 48, 2473.
10. M. Ikeuchi and M. Kihara, unpublished results.
11. T. A. Knoerzer, V. J. Watts, D. E. Nichols, and R. B. Mailman, J. Med. Chem., 1995, 38, 3062.
12. a) N. Sotomayor, E. Dominguez, and E. Lete, Tetrahedron, 1995, 51, 12721;
13. b) E. Dominguez, E. M. Marigorta, L. Carrillo, and R. Fenanas, Tetrahderon, 1991, 47, 9253.
14. M. Shimizu, H. Orita, T. Hayakawa, K. Suzuki, and K. Takehira, Heterocycles, 1995, 41, 773.
15. a) K. B. Wiberg, Chem. Rev., 1955, 55, 713;
16. b) F. H. Westheimer, Chem. Rev., 1961, 61, 265.
17. S. Sano, Y. Nagao, M. Ochiai, and E. Fujita, Tetrahedron, 1990, 46, 3211.
18. Y. Nagao, S. Sano, S. Nakagawa, M. Tanaka, and T. Taga, Chem. Lett., 1992, 915.
19. a) J. Knabe, J. Kubitz, and A. N. Ruppenthal, Angew. Chem., 1963, 75, 981;
20. b) J. Knabe and J. Kubitz, Arch. Pharmaz., 1964, 297, 129.
21. a) J. Knabe, R. Dorr, S. F. Dyke, and R. G. Kinsman, Tetrahedron Lett., 1972, 5373;
22. b) R. G. Kinsman, A. W. C. White, and S.F. Dyke, Tetarheron, 1975, 31, 449.
23. T. A. Geissman, "Organic Reactions: The Cannizzaro Reaction," Vol. II, ed. by R. Adams, John Wiley & Sons, Inc., New York, 1944, pp. 94-113.