Asymmetric rhodium carbene insertion into the Si-H bond: Identification of new dirhodium(II) carboxylate catalysts using parallel synthesis techniques

Tetrahedron Asymmetry

Volumn 14, Issue 7, 2003, Pages 791-816

  Buck, Richard T ^a,b   Coe, Diane M ^c   Drysdale, Martin J ^c   Ferris, Leigh ^a   Haigh, David ^c   Moody, Christopher J ^b   Pearson, Neil D ^c   Sanghera, J Bobby ^a  

^a LOUGHBOROUGH UNIVERSITY   (United Kingdom)

^b UNIVERSITY OF EXETER   (United Kingdom)

^c GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2 DIAZOPHENYLACETATE; ACETIC ACID DERIVATIVE; CARBENE; CARBOXYLIC ACID DERIVATIVE; DIRHODIUM CARBOXYLATE; RHODIUM; SILANE DERIVATIVE; SILICON; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; CHIRALITY; DECOMPOSITION; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGEN BOND; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; PRIORITY JOURNAL; SYNTHESIS; TECHNIQUE;

EID: 0037418805     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(03)00035-1     Document Type: Article

References (54)

1. Nozaki H., Moriuti S., Takaya H., Noyori R. Tetrahedron Lett. 7:1966;5239-5244.
2. Paulissen R., Reimlinger H., Hayez E., Hubert A.J., Teyssié P. Tetrahedron Lett. 14:1973;2233-2236.
3. Doyle M.P., McKervey M.A., Ye T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds. 1998;John Wiley, New York.
4. Doyle M.P., Forbes D.C. Chem. Rev. 98:1998;911-935.
5. Forbes D.C., McMills M.C. Curr. Org. Chem. 5:2001;1091-1105.
6. For recent examples, see: (a) Doyle, M. P.; Davies, S. B.; May, E. J. J. Org. Chem. 2001, 66, 8112-8119; (b) Doyle, M. P.; Hu, W. H.; Valenzuela, M. V. J. Org. Chem. 2002, 67, 2954-2959; (c) Davies, H. M. L.; Hansen, T.; Hopper, D. W.; Panaro, S. A. J. Am. Chem. Soc. 1999, 121, 6509-6510; (d) Davies, H. M. L.; Antoulinakis, E. G. Org. Lett. 2000, 2, 4153-4156.
7. For recent examples, see: (a) Doyle, M. P.; Davies, S. B.; May, E. J. J. Org. Chem. 2001, 66, 8112-8119; (b) Doyle, M. P.; Hu, W. H.; Valenzuela, M. V. J. Org. Chem. 2002, 67, 2954-2959; (c) Davies, H. M. L.; Hansen, T.; Hopper, D. W.; Panaro, S. A. J. Am. Chem. Soc. 1999, 121, 6509-6510; (d) Davies, H. M. L.; Antoulinakis, E. G. Org. Lett. 2000, 2, 4153-4156.
8. For recent examples, see: (a) Doyle, M. P.; Davies, S. B.; May, E. J. J. Org. Chem. 2001, 66, 8112-8119; (b) Doyle, M. P.; Hu, W. H.; Valenzuela, M. V. J. Org. Chem. 2002, 67, 2954-2959; (c) Davies, H. M. L.; Hansen, T.; Hopper, D. W.; Panaro, S. A. J. Am. Chem. Soc. 1999, 121, 6509-6510; (d) Davies, H. M. L.; Antoulinakis, E. G. Org. Lett. 2000, 2, 4153-4156.
9. For recent examples, see: (a) Doyle, M. P.; Davies, S. B.; May, E. J. J. Org. Chem. 2001, 66, 8112-8119; (b) Doyle, M. P.; Hu, W. H.; Valenzuela, M. V. J. Org. Chem. 2002, 67, 2954-2959; (c) Davies, H. M. L.; Hansen, T.; Hopper, D. W.; Panaro, S. A. J. Am. Chem. Soc. 1999, 121, 6509-6510; (d) Davies, H. M. L.; Antoulinakis, E. G. Org. Lett. 2000, 2, 4153-4156.
10. Brunner H., Wutz K., Doyle M.P. Monatsh. Chem. 121:1990;755-764.
11. García C.F., McKervey M.A., Ye T. J. Chem. Soc., Chem. Commun. 1996;1465-1466.
12. Miller D.J., Moody C.J. Tetrahedron. 51:1995;10811-10843.
13. Aller E., Brown D.S., Cox G.G., Miller D.J., Moody C.J. J. Org. Chem. 60:1995;4449-4460.
14. Ferris L., Haigh D., Moody C.J. Tetrahedron Lett. 37:1996;107-110.
15. Doyle M.P., Yan M. Tetrahedron Lett. 43:2002;5929-5931.
16. 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. 37:1996;7631-7634.
17. Buck R.T., Coe D.M., Drysdale M.J., Moody C.J., Pearson N.D. Tetrahedron Lett. 39:1998;7181-7184.
18. Bagheri V.B., Doyle M.P., Taunton J., Claxton E.E. J. Org. Chem. 53:1988;6158-6160.
19. Rijkens F., Janssen M.J., Drenth W., VanDerKerk G.J.M. J. Organometal. Chem. 2:1964;347-356.
20. Watanabe H., Kakano T., Araki K., Matsumoto H., Nagai Y. J. Organomet. Chem. 69:1974;389-396.
21. Baikov V.E., Danilkina L.P., Oglobin K.A. J. Gen. Chem. USSR. 51:1981;1858.
22. Andrey O., Landais Y., Planchenault D. Tetrahedron Lett. 34:1993;2927-2930.
23. Landais Y., Planchenault D. Tetrahedron Lett. 35:1994;4565-4568.
24. Landais Y., Planchenault D., Weber V. Tetrahedron Lett. 35:1994;9549-9552.
25. Andrey O., Landais Y., Planchenault D., Weber V. Tetrahedron. 51:1995;12083-12096.
26. Sengupta S., Das D., Sensarma D. Tetrahedron Lett. 37:1996;8815-8818.
27. Davies H.M.L., Hansen T., Rutberg J., Bruzinski P.R. Tetrahedron Lett. 38:1997;1741-1744.
28. Kitagaki S., Kinoshita M., Takeba M., Anada M., Hashimoto S. Tetrahedron: Asymmetry. 11:2000;3855-3859.
29. Dakin L.A., Schaus S.E., Jacobsen E.N., Panek J.S. Tetrahedron Lett. 39:1998;8947-8950.
30. Dakin L.A., Ong P.C., Panek J.S., Staples R.J., Stavropoulos P. Organometallics. 19:2000;2896-2908.
31. Landais Y., ParraRapado L., Planchenault D., Weber V. Tetrahedron Lett. 38:1997;229-232.
32. Bulugahapitiya P., Landais Y., ParraRapado L., Planchenault D., Weber V. J. Org. Chem. 62:1997;1630-1641.
33. Qu Z.H., Shi W.F., Wang J.B. J. Org. Chem. 66:2001;8139-8144.
34. Kennedy M., McKervey M.A., Maguire A.R., Roos G.H.P. J. Chem. Soc., Chem. Commun. 1990;361-362.
35. Agaskar P.A., Cotton F.A., Falvello L.R., Han S. J. Am. Chem. Soc. 108:1986;1214-1223.
36. Brunner H., Kluschanzoff H., Wutz K. Bull. Soc. Chim. Belg. 98:1989;63-72.
37. The structure of dirhodium(II) camphanate has been reported although no uses of it as a chiral catalyst were described. See: Kojic-Prodic B., Marcec R., Nigovic B., Raza Z., Sunjic V. Tetrahedron: Asymmetry. 3:1992;1-4.
38. Doyle M.P., Winchester W.R., Hoorn J.A.A., Lynch V., Simonsen S.H., Ghosh R. J. Am. Chem. Soc. 115:1993;9968-9978.
39. Doyle M.P., Hu W., Phillips I.M., Moody C.J., Pepper A.G., Slawin A.M.Z. Adv. Synth. Catal. 343:2001;112-117.
40. For example, see: (a) Reetz, M. T.; Becker, M. H.; Klein, H. W.; Stockigt, D. Angew. Chem., Int. Ed. 1999, 38, 1758-1761; (b) Dahmen, S.; Brase, S. Synthesis 2001, 1431-1449; (c) Chataigner, I.; Gennari, C.; Ongeri, S.; Piarulli, U.; Ceccarelli, S. Chem. Eur. J. 2001, 7, 2628-2634; (d) Reetz, M. T. Angew. Chem., Int. Ed. 2001, 40, 284-310.
41. For example, see: (a) Reetz, M. T.; Becker, M. H.; Klein, H. W.; Stockigt, D. Angew. Chem., Int. Ed. 1999, 38, 1758-1761; (b) Dahmen, S.; Brase, S. Synthesis 2001, 1431-1449; (c) Chataigner, I.; Gennari, C.; Ongeri, S.; Piarulli, U.; Ceccarelli, S. Chem. Eur. J. 2001, 7, 2628-2634; (d) Reetz, M. T. Angew. Chem., Int. Ed. 2001, 40, 284-310.
42. For example, see: (a) Reetz, M. T.; Becker, M. H.; Klein, H. W.; Stockigt, D. Angew. Chem., Int. Ed. 1999, 38, 1758-1761; (b) Dahmen, S.; Brase, S. Synthesis 2001, 1431-1449; (c) Chataigner, I.; Gennari, C.; Ongeri, S.; Piarulli, U.; Ceccarelli, S. Chem. Eur. J. 2001, 7, 2628-2634; (d) Reetz, M. T. Angew. Chem., Int. Ed. 2001, 40, 284-310.
43. For example, see: (a) Reetz, M. T.; Becker, M. H.; Klein, H. W.; Stockigt, D. Angew. Chem., Int. Ed. 1999, 38, 1758-1761; (b) Dahmen, S.; Brase, S. Synthesis 2001, 1431-1449; (c) Chataigner, I.; Gennari, C.; Ongeri, S.; Piarulli, U.; Ceccarelli, S. Chem. Eur. J. 2001, 7, 2628-2634; (d) Reetz, M. T. Angew. Chem., Int. Ed. 2001, 40, 284-310.
44. Roos G.H.P., McKervey M.A. Synth. Commun. 22:1992;1751-1756.
45. Davies H.M.L. Aldrichim. Acta. 1997;107-114.
46. Davies H.M.L. Eur. J. Org. Chem. 1999;2459-2469.
47. Hashimoto S., Watanabe N., Ikegami D. Tetrahedron Lett. 31:1990;5173-5174.
48. Buck, R. T.; Moody, C. J.; Pepper, A. G. ARKIVOC 2002, 16-32. http://arkat-usa.org/ark/journal/2002/Padwa/AP-2391H/2391H.htm.
49. Landais Y., Planchenault D. Tetrahedron. 53:1997;2855-2870.
50. Regitz M., Maas G. Diazo Compounds. Properties and Synthesis. 1986;Academic Press, Orlando, FL.
51. Höfle G., Steglich W. Synthesis. 1972;619-621.
52. Smith H.E., Orr R.K., Chen F.-M. J. Am. Chem. Soc. 97:1975;3126-3130.
53. McKenzie A. J. Chem. Soc. 75:1899;753-770.
54. Kotsuki H., Kataoka M., Nishizawa H. Tetrahedron Lett. 34:1993;4031-4034.