One-pot, cis-selective synthesis of α-substituted β-trimethylsilyl-α,β-epoxyesters from α-ketoesters and diazo(trimethylsilyl)methyl magnesium bromide

Tetrahedron Letters

Volumn 47, Issue 12, 2006, Pages 1977-1980

  Hari, Yoshiyuki ^a   Tsuchida, Susumu ^a   Aoyama, Toyohiko ^a  

^a NAGOYA CITY UNIVERSITY   (Japan)

Author keywords

Ketoesters; Epoxyesters; Glycidates; One pot synthesis; Trimethylsilyldiazomethane

Indexed keywords

BROMINE DERIVATIVE; DIAZO(TRIMETHYLSILYL)METHYL MAGNESIUM BROMIDE; EPOXIDE; ESTER DERIVATIVE; PIVALIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CIS ISOMER; DIASTEREOISOMER; PROTON TRANSPORT; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 32644466551     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.01.067     Document Type: Article

References (53)

1. K. Eistetter, and H.P.O. Wolf J. Med. Chem. 25 1982 109 113
2. T.C. Kiorpes, D. Hoerr, W. Ho, L.E. Weaner, M.G. Inman, and G.F. Tutwiler J. Biol. Chem. 259 1984 9750 9755
3. W. Ho, G.F. Tutwiler, S.C. Cottrell, D.J. Morgans, O. Tarhan, and R.J. Mohrbacher J. Med. Chem. 29 1986 2184 2190
4. J.G. Bauman, R.C. Hawley, and H. Rapoport J. Org. Chem. 49 1984 3791 3796
5. R. Takagi, J. Kimura, Y. Shinohara, Y. Ohba, K. Takezono, Y. Hiraga, S. Kojima, and K. Ohkata J. Chem. Soc., Perkin Trans. 1 1998 689 698
6. J. Wehbe, T. Kassem, V. Rolland, M. Rolland, M. Tabcheh, M.-L. Roumestant, and J. Martinez Org. Biomol. Chem. 1 2003 1938 1942
7. R.W. White, and W.D. Emmons Tetrahedron 17 1962 31 34
8. C.P. Whitman, J.C. Craig, and G.L. Kenyon Tetrahedron 41 1985 1183 1192
9. C. Clark, P. Hermans, O. Meth-Cohn, C. Moore, H.C. Taljaard, and G. Van Vuuren J. Chem. Soc., Chem. Commun. 1986 1378 1380
10. A. Foucaud, and M. Bakouetila Synthesis 1987 854 856
11. B. Tarnchompoo, C. Thebtaranonth, and Y. Thebtaranonth Tetrahedron Lett. 28 1987 6671 6674
12. W. Ho, O. Tarhan, T.C. Kiorpes, G.F. Tutwiler, and R.J. Mohrbacher J. Med. Chem. 30 1987 1094 1097
13. W. Adam, L. Hadjiarapoglou, and B. Nestler Tetrahedron Lett. 31 1990 331 334
14. A. Foucaud, and E. Le Rouille Synthesis 1990 787 789
15. W. Foestl, S.J. Michel, G. von Sprecher, P.J. Diel, R.G. Hall, L. Maier, D. Strub, V. Melillo, P.A. Baumann, R. Bernasconi, C. Gentsch, K. Hauser, J. Jaekel, G. Karlsson, K. Klebs, L. Maître, C. Marescaux, M.F. Pozza, M. Schmutz, M.W. Steinmann, H. van Riezen, A. Vassout, C. Mondadori, H.-R. Olpe, P.C. Waldmeier, and H. Bittiger J. Med. Chem. 38 1995 3313 3331
16. Y.-G. Suh, K.-H. Min, S.-Y. Baek, and J.-H. Chai Heterocycles 48 1998 1527 1535
17. D. Basavaiah, and N. Kumaragurubaran Tetrahedron Lett. 42 2001 477 479
18. Y. Iwabuchi, M. Furukawa, T. Esumi, and S. Hatakeyama Chem. Commun. 2001 2030 2031
19. Y. Iwabuchi, T. Sugihara, T. Esumi, and S. Hatakeyama Tetrahedron Lett. 42 2001 7867 7871
20. C. Navarro, M. Deguel-Castaing, D. Colombani, and B. Maillard Synlett 1992 587 588
21. M. Deguel-Castaing, C. Navarro, R. Ferdinando, and B. Maillard Aust. J. Chem. 48 1995 233 240
22. C. Cramay, R. Ferdinando, M. Deguel-Castaing, and B. Maillard Chem. Commun. 1998 1855 1856
23. C. Cramay, M. Deguel-Castaing, and B. Maillard J. Chem. Soc., Perkin Trans. 1 1999 3573 3577
24. C. Cramay, M. Deguel-Castaing, and B. Maillard J. Org. Chem. 66 2001 3492 3494
25. Other synthetic methods. L. Thijs, L.M. Smeets, P.J.M. Cillissen, J. Harmsen, and B. Zwanenburg Tetrahedron 36 1980 2141 2143
26. W. Adam, A. Griesbeck, and E. Staab Angew. Chem., Int. Ed. 25 1986 269 270
27. W. Adam, A. Griesbeck, and E. Staab Tetrahedron Lett. 27 1986 2839 2842
28. M.M.L. Crilley, A.J.F. Edmunds, K. Eistetter, and B.T. Golding Tetrahedron Lett. 30 1989 885 888
29. M. Díaz, J. Ibarzo, and R.M. Ortuño Tetrahedron: Asymmetry 5 1994 37 40
30. T. Früh, and G.M. Ramos Tombo Synlett 1994 727 728
31. J.L. García Ruano, A.M. Martín Castro, and J.H. Rodríguez J. Org. Chem. 59 1994 533 536
32. A. Arnone, P. Bravo, M. Frigerio, G. Salani, and F. Viani Tetrahedron 50 1994 13485 13492
33. M. Díaz, V. Branchadell, A. Oliva, and R.M. Ortuño Tetrahedron 51 1995 11841 11854
34. S.-S. Jew, H.-O. Kim, B.-S. Jeong, and H.-G. Park Tetrahedron: Asymmetry 8 1997 1187 1192
35. O. Jimenez, M.P. Bosch, and A. Guerrero J. Org. Chem. 62 1997 3496 3499
36. S.-S. Jew, E.-K. Kim, S.-M. Je, L.-X. Zhao, H.-G. Park, K.-H. Ko, W.-K. Kim, H.-J. Kim, J.-H. Cheong, and E.-S. Lee Heterocycles 52 2000 1087 1103
37. S.-S. Jew, E.-Y. Roh, E.-Y. Baek, L. Mireille, H.-O. Kim, B.-S. Jeong, M.-K. Park, and H.-G. Park Tetraherdon: Asymmetry 11 2000 3395 3401
38. H.M.L. Davies, and J. DeMeese Tetrahedron Lett. 42 2001 6803 6805
39. R.J. Cox, J. Durston, and D.I. Roper J. Chem. Soc., Perkin Trans. 1 2002 1029 1035
40. C.-D. Lu, Z.-Y. Chen, H. Liu, W.-H. Hu, and A.-Q. Mi Org. Lett. 6 2004 3071 3074
41. A.E. Russell, J. Brekan, L. Gronenberg, and M.P. Doyle J. Org. Chem. 69 2004 5269 5274
42. Y. Hari, S. Tanaka, Y. Takuma, and T. Aoyama Synlett 2003 2151 2154
43. S. Tsuchida, Y. Hari, and T. Aoyama Heterocycles 65 2005 2667 2674
44. U. Schöllkopf, and H.-U. Scholz Synthesis 1976 271 272
45. 2. H. Ogawa, T. Aoyama, and T. Shioiri Heterocycles 42 1996 75 82
46. Spectroscopic data of the crude product showed the presence of 1,3-Brook rearrangement product formed by the intermediate 3a-Li.
47. 2O), 4.20-4.29 (m, 2H), 7.17-7.31 (m, 5H).
48. 4, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (BW-200MH, 10 g, hexane-EtOAc = 30:1) to afford 4a (125 mg, 88%, cis:trans = 96:4).
49. The stereochemistry of the compounds 4 was determined by NOESY measurement.
50. 3) δ: 0.24 (s, 9H), 1.53 (s, 9H), 2.76 (s, 1H), 7.31-7.34 (m, 3H), 7.43-7.46 (m, 2H).
51. C. Burford, F. Cooke, E. Ehlinger, and P. Magnus J. Am. Chem. Soc. 99 1977 4536 4537
52. C. Burford, F. Cooke, G. Roy, and P. Magnus Tetrahedron 39 1981 867 876
53. 4, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (BW-200MH, 6 g, hexane-EtOAc = 30:1) to afford 4a (77 mg, 54%, cis:trans = 32:68).