Studies on the Rh(II)-catalyzed C-H insertion reaction of some derivatives of N-[4-{(S)-1,2-dihydroxybutyl}]-α-diazoanilides: Site- selectivity

Heterocycles

Volumn 53, Issue 3, 2000, Pages 637-655

  Wee, Andrew G H ^a   McLeod, Douglas D ^a  

^a UNIVERSITY OF REGINA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; ANILIDE; AZO COMPOUND; RHODIUM;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; PURIFICATION; STEREOCHEMISTRY;

EID: 0034163024     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-99-8805     Document Type: Article

References (20)

1. (a) A. G. H. Wee, B.-S. Liu, and D. D. McLeod, J. Org. Chem., 1998, 63, 4218. (b) A. G. H. Wee and B.-S. Liu, Tetrahedron Lett., 1996, 37, 145.
2. (a) A. G. H. Wee, B.-S. Liu, and D. D. McLeod, J. Org. Chem., 1998, 63, 4218. (b) A. G. H. Wee and B.-S. Liu, Tetrahedron Lett., 1996, 37, 145.
3. Other related studies: (a) M. Anada and S.-i. Hashimoto, Tetrahedron Lett., 1998, 39, 79. (b) M. P. Doyle, M. N. Protopopova, W. R. Winchester, and K. L. Daniel, Tetrahedron Lett., 1992, 33, 7819.
4. Other related studies: (a) M. Anada and S.-i. Hashimoto, Tetrahedron Lett., 1998, 39, 79. (b) M. P. Doyle, M. N. Protopopova, W. R. Winchester, and K. L. Daniel, Tetrahedron Lett., 1992, 33, 7819.
5. (a) D. F. Taber, K. K. You, and A. Rheingold, J. Am. Chem. Soc., 1996, 118, 547. (b) D. F. Taber and Y. Song, J. Org. Chem., 1996, 61, 6706. (c) T. Yakura, S. Yamada, A. Ueki, and M. Ikeda, Synlett, 1997, 185.
6. (a) D. F. Taber, K. K. You, and A. Rheingold, J. Am. Chem. Soc., 1996, 118, 547. (b) D. F. Taber and Y. Song, J. Org. Chem., 1996, 61, 6706. (c) T. Yakura, S. Yamada, A. Ueki, and M. Ikeda, Synlett, 1997, 185.
7. (a) D. F. Taber, K. K. You, and A. Rheingold, J. Am. Chem. Soc., 1996, 118, 547. (b) D. F. Taber and Y. Song, J. Org. Chem., 1996, 61, 6706. (c) T. Yakura, S. Yamada, A. Ueki, and M. Ikeda, Synlett, 1997, 185.
8. S. Saito, T. Hasegawa, M. Inaba, R. Nishida, T. Fujii, S. Nomizu, and T. Moriwake, Chem. Lett., 1984, 1389.
9. B. Neises and W. Steglich, Angew. Chem., Int. Ed. Engl., 1978, 17, 522.
10. D. F. Taber, R. E. Ruckle, Jr., and M. J. Hennesy, J. Org. Chem., 1986, 51, 4077.
11. A. G. H. Wee, B.-S. Liu, and L. Zhang, J. Org. Chem., 1992, 57, 4404.
12. S.-i. Hashimoto, N. Watanabe, M. Anada, and S. Ikegami, J. Synth. Org. Chem, Jpn., 1996, 54, 114.
13. M. P. Doyle, V. Bagheri, M. M. Pearson, and J. D. Edwards, Tetrahedron Lett., 1989, 30, 7001.
14. 1H NMR δ: 1.27 (s, 3H, Me), 1.35 (s, 3H, Me), 1.86 (ddd, 1H, J= 14.3, 8.9, 3.5 Hz, CH'), 2.23 (ddd, 1H, J = 14.3, 8.4, 2.7 Hz, CH'), 3.48 ("t", 1H, J = 7.4 Hz, H-3'), 3.72 (s, 6H, OMe), 3.97 (dd, 1H, J = 7.4, 5.9 Hz, H-3'), 4.01 (d, 1H, J = 2.2 Hz, H-3), 4.03-4.21 (m, 1H, H-2'). 4.47 (dt, 1H, J = 2.2, 8.8 Hz, H-4), 6.81 (d, 2H, J = 9.2 Hz, ArH), 7.22 (d, 2H, J = 9.2 Hz, ArH).
15. (a) K. D. Barrow and T. M. Spotwood, Tetrahedron Lett., 1965, 3325. (b) H. B. Kagan, J. J. Basselier, and J. L. Luche, Tetrahedron Lett., 1964, 941.
16. (a) K. D. Barrow and T. M. Spotwood, Tetrahedron Lett., 1965, 3325. (b) H. B. Kagan, J. J. Basselier, and J. L. Luche, Tetrahedron Lett., 1964, 941.
17. J. R. Rasmussen, J. Org. Chem., 1980, 45, 2725.
18. J. Eustache, A. Grob, C. Lam, O. Sellier, and G. Schulz, Bioorg. Med. Chem. Lett., 1998, 8, 2961.
19. M. J. Robins and P. J. Wilson, J. Am. Chem. Soc., 1981, 103, 932.
20. W. C. Still, M. Kahn, and A. Mitra, J. Org. Chem., 1978, 43, 2923.