Enantioselective carbometallation of unactivated olefins

Abstract

Covering: until September 1998

References

1. K. Ziegler and K. Bähr, Chem. Ber., 1928, 61, 253.
2. M. Morton, Anionic polymerization: Principles and Practice, Academic Press, N.Y., 1983.
3. P. Knochel, Comprehensive Organic Synthesis, eds. B. Trost and I. Fleming, Pergamon Press, New York, 1991, 4, 865.
4. I. Marek and J. F. Normant, Carbometallation Reactions, Cross Coupling Reactions, eds. P. J. Stang and F. Diederich, Wiley-VCH, Weinheim, 1998, p. 271.
5. (a) E.-I. Negishi, Pure Appl. Chem., 1981, 53, 2333; (b) E.-I. Neghishi, D. Y. Kondakov, D. Choueiry, K. Kasai and T. Takahashi, J. Am. Chem. Soc., 1996, 118, 9577.
6. (a) F. R. W. P. Wild, H. Wasiucionek, G. Huttner and H. Brintzinger, J. Organomet. Chem., 1985, 288, 63; (b) B. Chin and S. L. Buckwald, J. Org. Chem., 1997, 62, 2267.
7. A. H. Hoveyda and J. P. Morken, J. Org. Chem., 1993, 58, 4237.
8. (a) J. P. Morken, M. T. Didiuk and A. H. Hoveyda, J. Am. Chem. Soc., 1993, 115, 6997; (b) M. S. Visser, N. M. Heron, M. T. Didiuk, J. F. Sagal and A. H. Hoveyda, J. Am. Chem. Soc., 1996, 118, 4291; (c) A. H. Hoveyda and J. P. Morken, Angew. Chem., Int. Ed. Engl., 1996, 35, 1262.
9. (a) A. F. Houri, Z. Xu, D. A. Cogan and A. H. Hoveyda, J. Am. Chem. Soc., 1995, 117, 2943; (b) Z. Xu, C. W. Johannes, A. F. Houri, D. S. La, D. A. Cogan, G. E. HoWnela and A. H. Hoveyda, J. Am. Chem. Soc., 1997, 119, 10302.
10. (a) J. P. Morken, M. T. Didiuk, M. S. Visser and A. H. Hoveyda, J. Am. Chem. Soc., 1994, 116, 3123; (b) M. S. Visser and A. H. Hoveyda, Tetrahedron, 1995, 51, 4383.
11. (a) S. M. Visser, J. P. A. Harrity and A. H. Hoveyda, J. Am. Chem. Soc., 1996, 118, 3779; (b) C. W. Johannes, M. S. Visser, G. S. Weatherhead and A. H. Hoveyda, J. Am. Chem. Soc., 1998, 120, 8340.
12. Reaction of racemic allylic alcohol and 10 mol% of racemic complex 2 affords the product with little selectivity.
13. L. Bell, R. J. Whitby, R. J. Jones and M. C. H. Standen, Tetrahedron Lett., 1996, 37, 7139.
14. D. Y. Kondakov and E.-I. Negishi, J. Am. Chem. Soc., 1995, 117, 10771.
15. D. Y. Kondakov and E.-I. Negishi, J. Am. Chem. Soc., 1996, 118, 1577.
16. G. Dawson, C. A. Durrant, G. G. Kirk, R. J. Whitby, R. V. H. Jones and M. C. H. Standen, Tetrahedron Lett., 1997, 38, 2335.
17. (a) H. Felkin, A. Swierczewski and A. Tambute, Tetrahedron Lett., 1969, 707; (b) J. K. Crandall and A. C. Clark, J. Org. Chem., 1972, 37, 4236.
18. S. Klein, I. Marek, J. F. Poisson and J. F. Normant, J. Am. Chem. Soc., 1995, 117, 8853.
19. T. Kato, T. Marumoto, I. Sato and I. Kuwajima, Synlett, 1991, 671.
20. For a mechanistic discussion on the stereochemical outcome of benzylic organolithium derivatives, see: C. M. Lichtenfeld and H. Ahlbrecht, Tetrahedron, 1996, 52, 10025.
21. The reaction was perfomed on a 50 mmol scale of cinnamyl alcohol in the presence of 5% sparteine. However, in this case a slightly lower yield is obtained due to the telomerization of 11Li on cinnamyl alcoholate leading to a dimer.
22. K. N. Houk, N. G. Rondan, P. v. R. Schleyer, E. Kaufmann and T. Clark, J. Am. Chem. Soc., 1985, 107, 2821.
23. W. F. Bailey, A. D. Khanolkar, K. Gavaskar, T. V. Ovaska, K. Rossi, Y. Thiel and K. B. Wiberg, J. Am. Chem. Soc., 1991, 113, 5720.
24. (a) J. P. Oliver, J. B. Smart and M. T. Emerson, J. Am. Chem. Soc., 1966, 88, 4101; (b) J. St. Denis and J. P. Oliver, J. Am. Chem. Soc., 1972, 94, 8260; (c) T. W. Dolzine and J. P. Oliver, J. Organomet. Chem., 1974, 78, 165; (d) J. St. Denis, J. P. Oliver, J. B. Smart and T. W. Dolzine, J. Organomet. Chem., 1974, 78, 165.
25. P. Beak and A. I. Meyers, Acc. Chem. Res., 1986, 19, 356.
26. S. Norsikian, I. Marek, J.-F. Poisson and J. F. Normant, J. Org. Chem., 1997, 62, 4898.
27. (a) A. Alexakis, J. C. Frutos, S. Mutti and P. Mangeney, J. Org. Chem., 1994, 59, 3326; (b) A. Alexakis, S. Mutti and P. Mangeney, J. Org. Chem., 1992, 57, 1224.
28. For a highlight see C. Bolm, F. Bienewald and A. Seger, Angew. Chem., Int. Ed. Engl., 1996, 35, 1657 and references cited therein.
29. The formation of cyclopropane by 1,3-elimination between an organo-gem-bismetallic and a methoxymethyl ether has already been described: (a) I. Marek, D. Beruben and J. F. Normant, Tetrahedron Lett., 1995, 36, 3695; (b) D. Beruben, I. Marek, J. F. Normant and N. Platzer, J. Org. Chem., 1995, 60, 2488; (c) D. Beruben, I. Marek, J. F. Normant and N. Platzer, Tetrahedron Lett., 1993, 34, 7575.
30. For some representative formations of chiral cyclopropanes, see (a) A. B. Charette and J. F. Marcoux, Synlett, 1995, 1197 and references cited therein; (b) J. Salaün, Chem. Rev., 1989, 89, 1247; (c) D. Romo and A. I. Meyers, J. Org. Chem., 1992, 57, 6265; (d) H. M. L. Davies, N. J. S. Huby, W. R. Cantrell Jr. and J. L. Olive, J. Am. Chem. Soc., 1993, 115, 9468; (e) M. P. Doyle, in Catalytic Asymmetric Synthesis, ed. I. Ojima, VCH Publishers, New York, 1993, ch. 3; (f) A. Pfaltz, Acc. Chem. Res., 1993, 26, 339; (g) D. A. Evans, K. A. Woerpel and M. J. Scott, Angew. Chem., Int. Ed. Engl., 1992, 31, 430; (h) S. E. Denmark and S. P. O'Connor, J. Org. Chem., 1997, 62, 584.
31. A. Krief and M. Hobe, Tetrahedron Lett., 1992, 33, 6529.
32. (a) A. Krief and M. Hobe, Tetrahedron Lett., 1992, 33, 6527; (b) A. Krief, M. Hobe, W. Dumont, E. Badaoui, E. Guittet and G. Evrard, Tetrahedron Lett., 1992, 33, 3381.
33. For a previous report on the synthesis of chiral cyclopropane mediated by a stoichiometric amount of (–)-sparteine, see M. Paetow, M. Kotthaus, M. Grehl, R. Frölich and D. Hoppe, Synlett, 1994, 1034.
34. (a) X. Wei and R. J. K. Taylor, Tetrahedron: Asymmetry, 1997, 8, 665; (b) X. Wei and R. J. K. Taylor, Tetrahedron Lett., 1996, 37, 4209; (c) X. Wei and R. J. K. Taylor, Chem. Commun., 1996, 187; (d) K. G. Richey Jr., A. S. Heyn and W. F. Erickson, J. Org. Chem., 1983, 48, 3821; (e) S. Superchi, N. Sotomayor, G. Miao, B. Joseph, M. G. Campbell and V. Snieckus, Tetrahedron Lett., 1996, 37, 6061.
35. S. Norsikian, I. Marek and J. F. Normant, Tetrahedron Lett., 1997, 43, 7523.
36. (a) M. J. Woltering, R. Frohlich and D. Hoppe, Angew. Chem., Int. Ed. Engl., 1997, 36, 1764; (b) D. Hoppe and T. Hense, Angew. Chem., Int. Ed. Engl., 1997, 36, 2282; (c) M. Oestreich, R. Frohlich and D. Hoppe, Tetrahedron Lett., 1998, 39, 1745; (d) M. J. Woltering, R. Frohlich, B. Wibbeling and D. Hoppe, Synlett, 1998, 797.
37. K. Tomooka, N. Komine and T. Nakai, Tetrahedron Lett., 1997, 38, 8939.
38. (a) K. Tomooka, T. Igarashi, N. Komine and T. Nakai, Tetrahedron Lett., 1992, 33, 5795; (b) K. Tomooka, T. Igarashi and T. Nakai, Tetrahedron, 1994, 50, 5927.
39. S. T. Kerrick and P. Beak, J. Am. Chem. Soc., 1991, 113, 9708.
40. I. Coldham, R. Hufton and D. J. Snowden, J. Am. Chem. Soc., 1996, 118, 5322.
41. A. Krief and J. Bousbaa, Synlett, 1996, 1007.
42. Without LiBr, the diastereomeric ratio is lower.
43. I. Coldham, R. Hufton and R. E. Rathmell, Tetrahedron Lett., 1997, 38, 7617.
44. M. Isaka and E. Nakamura, J. Am. Chem. Soc., 1990, 112, 7428.
45. K. Kubota, M. Nakamura, M. Isaka and E. Nakamura, J. Am. Chem. Soc., 1993, 115, 5867.
46. (a) M. Nakamura, M. Arai and E. Nakamura, J. Am. Chem. Soc., 1995, 117, 1179; (b) E. Nakamura, Pure Appl. Chem., 1996, 68, 123.
47. E. Lorthiois, I. Marek and J. F. Normant, Tetrahedron Lett., 1997, 38, 89.
48. P. Karoyan and G. Chassaing, Tetrahedron Lett., 1997, 38, 85.
49. Y. Gao and F. Sato, J. Org. Chem., 1995, 60, 8136.
50. E. Lorthiois, I. Marek and J. F. Normant, J. Org. Chem., 1998, 63, 2442.
51. E. Nakamura and K. Kubota, J. Org. Chem., 1997, 62, 792.
52. K. Kubota and E. Nakamura, Angew. Chem., Int. Ed. Engl., 1997, 36, 2491.
53. I. Marek and J. F. Normant, Chem. Rev., 1996, 96, 3241.
54. D. Brasseur, H. Rezaei, A. Fuxa, A. Alexakis, P. Mangeney, I. Marek and J. F. Normant, Tetrahedron Lett., 1998, 39, 4821.
55. S. G. Davies, O. Ichihara and I. A. S. Walters, Synlett, 1993, 461.
56. D. Brasseur, I. Marek and J. F. Normant, C. R. Seances Acad. Sci., Ser. II, 1998, 621.
57. I. Marek, C. Meyer and J. F. Normant, Org. Synth., 1995, 74, 194.
58. For a general review on aminals in asymmetric synthesis see A. Alexakis and P. Mangeney, Advanced Asymmetric Synthesis, ed. G. R. Stephenson, Chapman & Hall, London, 1996, p. 93.
59. A. Alexakis, N. Lensen, J. P. Tranchier and P. Mangeney, J. Org. Chem., 1992, 57, 4563.