An unusual observation in the rhodium carbenoids: [1,4]-migration in the sugar-derived α-diazo-β-ketoesters

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 2, 2000, Pages 147-151

  Desai, Vijaya N ^a   Saha, Nabendu N ^a   Dhavale, Dilip D ^a  

^a UNIVERSITY OF PUNE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTICS; CATALYSIS; CHEMICAL BONDS; CHROMATOGRAPHY; DERIVATIVES; INFRARED RADIATION; NUCLEAR MAGNETIC RESONANCE; POLYETHERS; PROTONS; RHODIUM COMPOUNDS; SUBSTRATES; SUGAR (SUCROSE); SYNTHESIS (CHEMICAL);

COMPLEX MIXTURES;

ESTERS;

EID: 0034695706     PISSN: 14704358     EISSN: None     Source Type: Journal    
DOI: 10.1039/a908453c     Document Type: Article

References (22)

1. J. Adams and D. M. Spero, Tetrahedron, 1991, 47, 1765;
2. A. Padwa and K. E. Krumpe, Tetrahedron, 1992, 48, 5385;
3. T. Ye and M. A. McKervey, Chem. Rev, 1994, 94, 1091;
4. D. J. Miller and C. J. Moody, Tetrahedron, 1995, 51, 10811;
5. A. Padwa and M. D. Weingarten, Chem. Rev., 1996, 96, 223;
6. G. A. Sulikowski, K. L. Cha and M. M. Sulikowski, Tetrahedron: Asymmetry, 1998, 9, 3145;
7. M. P. Doyle and D. C. Forbes, Chem. Rev., 1998, 98, 911.
8. (a) M. C. Pirrung and J. A. Werner, J. Am. Chem. Soc., 1986, 108, 6060;
9. M. P. Doyle, V. Bagheri and N. K. Harn, Tetrahedron Lett., 1988, 29, 5119;
10. E. J. Roskamp and C. R. Johnson, J. Am. Chem. Soc., 1986, 108, 6062;
11. (b) J. S. Clark, Tetrahedron Lett., 1992, 33, 6193;
12. T. Ye, C. F. Garcia and M. A. McKervey, J. Chem. Soc., Perkin Trans. 1, 1995, 1373.
13. J. B. Brogan, C. B. Bauer, R. D. Rogers and C. K. Zercher, Tetrahedron Lett., 1996, 37, 5053;
14. M. P. Doyle, D. G. Ene, D. C. Forbes and J. S. Tedrow, Tetrahedron Lett., 1997, 38, 4367.
15. For prior reports of minor amounts of [1,4]-shift products in rearrangements of sulfonium and ammonium ylides see: J. E. Baldwin, W. F. Erickson, R. E. Hackler and R. M. Scott, J. Chem. Soc., Chem. Commun., 1970, 576;
16. K. Chantrapromma, W. D. Ollis and I. O. Sutherland, J. Chem. Soc., Perkin Trans. 1, 1983, 1049.
17. M. C. Pirrung, W. L. Brown, S. Rege and P. Laughton, J. Am. Chem. Soc., 1991, 113, 8561.
18. F. G. West, B. N. Naidu and R. W. Tester, J. Org. Chem., 1994, 59, 6892.
19. (a) D. D. Dhavale, N. N. Bhujbal, P. Joshi and S. G. Desai, Carbohydr. Res., 1994, 263, 303;
20. (b) D. D. Dhavale, N. N. Sana and V. N. Desai, J. Org. Chem., 1997, 62, 7482;
21. N. N. Saha, V. N. Desai and D. D. Dhavale, J. Org. Chem., 1999, 64, 1715.
22. Analogous experimental evidence for rotational degree of freedom in rhodium carbeniods is known. See: D. F. Taber and S. C. Malcolm, J. Org. Chem., 1998, 63, 3717.