Parallel synthesis techniques in the identification of new chiral dirhodium(II) carboxylates for asymmetric carbenoid insertion reactions

Tetrahedron Letters

Volumn 39, Issue 39, 1998, Pages 7181-7184

  Buck, Richard T ^a   Coe, Diane M ^b   Drysdale, Martin J ^b   Moody, Christopher J ^a   Pearson, Neil D ^b  

^a UNIVERSITY OF EXETER   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; RHODIUM DERIVATIVE;

ARTICLE; CHIRALITY; DRUG INDUSTRY; DRUG SYNTHESIS; DRUG USE; LIGAND BINDING;

EID: 0032563851     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01538-X     Document Type: Article

References (19)

1. 1. Burgess, K.; Moye-Sherman, D.; Porte, A. M. Molecular Diversity and Combinatorial Chemistry: Libraries and Drug Discovery, Eds: Chaiken, I. M.; Janda, K. D. Publisher: American Chemical Society, Washington, D.C., 1996, pp. 128-136
2. 2. (a) Burgess, K.; Lim, H-J.; Porte, A. M.; Sulikowski, G. A. Angew. Chem. Int. Ed. Engl. 1996, 35, 220-222;
3. (b) Gao, X.; Kagan, H. B. Chirality 1998, 10, 120-124.
4. 3. Francis, M. B.; Finney, N. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 8983-8984.
5. 4. (a) Xiang, X.-D; Sun, X.-D.; Briceno, G.; Lou, Y.-L.; Wang, K. A.; Chang, H. Y.; Wallace-Freedman, W. G.; Chen, S.-W.; Schultz, P. G. Science 1995, 268, 1738-1740;
6. (b) Sun, X.-D.; Wang, K. A.; Yoo, Y.; Wallace-Freedman, W. G.; Gao, C.; Xiang, X. D.; Schultz, P. G. Adv. Mater. 1997, 9, 1046.
7. 5. (a) Liu, G.-C.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712-7713;
8. (b) Cole, B. M.; Shimizu, K. D.; Krueger, C. A.; Harrity, J. P. A.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem. Int. Ed. Engl. 1996, 35, 1668-1671;
9. (c) Gilbertson, S. R.; Wang, X. Tetrahedron Lett. 1996, 37, 6475-6478;
10. (d) Shimizu, K. D.; Cole, B. M.; Krueger, C. A.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem. Int. Ed. Engl. 1997, 36, 1704-1707.
11. 6. For other work on Si-H insertion reactions of carbenes and carbenoids, see: ref. 8 and references therein, and Bulugahapitiya, P.; Landais, Y.; ParraRapado, L.; Planchenault, D.; Weber, V. J. Org. Chem. 1997, 62, 1630-1641; Landais, Y.; ParraRapado, L.; Planchenault, D.; Weber, V. Tetrahedron Lett. 1997, 38, 229-232; Landais, Y.; Planchenault, D. Tetrahedron 1997, 53, 2855-2870.
12. 6. For other work on Si-H insertion reactions of carbenes and carbenoids, see: ref. 8 and references therein, and Bulugahapitiya, P.; Landais, Y.; ParraRapado, L.; Planchenault, D.; Weber, V. J. Org. Chem. 1997, 62, 1630-1641; Landais, Y.; ParraRapado, L.; Planchenault, D.; Weber, V. Tetrahedron Lett. 1997, 38, 229-232; Landais, Y.; Planchenault, D. Tetrahedron 1997, 53, 2855-2870.
13. 6. For other work on Si-H insertion reactions of carbenes and carbenoids, see: ref. 8 and references therein, and Bulugahapitiya, P.; Landais, Y.; ParraRapado, L.; Planchenault, D.; Weber, V. J. Org. Chem. 1997, 62, 1630-1641; Landais, Y.; ParraRapado, L.; Planchenault, D.; Weber, V. Tetrahedron Lett. 1997, 38, 229-232; Landais, Y.; Planchenault, D. Tetrahedron 1997, 53, 2855-2870.
14. 7. Doyle, M. P.; McKervey, M. A.; Ye, T. 'Modern Catalytic Methods for Organic Synthesis with Diazo Compounds', John Wiley, New York, 1998; Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911-935.
15. 7. Doyle, M. P.; McKervey, M. A.; Ye, T. 'Modern Catalytic Methods for Organic Synthesis with Diazo Compounds', John Wiley, New York, 1998; Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911-935.
16. 8. Buck, R. T.; Doyle, M. P.; Drysdale, M. J.; Ferris, L.; Forbes, D. C.; Haigh, D.; Moody, C. J.; Pearson, N. D.; Zhou, Q.-L. Tetrahedron Lett. 1996, 37, 7631-7634.
17. 9. Subsequent work by Davies, showed that improved enantioselectivity could be attained using proline based catalysts: Davies, H. M. L.; Hansen, T.; Rutberg, J.; Bruzinski, P. R. Tetrahedron Lett. 1997, 38, 1741-1744.
18. 10. Roos, G. H. P.; McKervey, M. A. Synth. Commun. 1992, 22, 1751-1756.
19. 11. Chiralpak AD column, 0.5% 2-propanol in hexane, or Whelk-O column, 5% ethyl acetate in heptane.