Regio- and enantioselective substitution of acyclic allylic sulfoximines with butylcopper in the presence of lithium iodide and boron trifluoride

Journal of Organic Chemistry

Volumn 61, Issue 13, 1996, Pages 4379-4390

  Scommoda, Matthias ^a   Gais, Hans Joachim ^a   Bosshammer, Stephan ^a   Raabe, Gerhard ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001095187     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960027u     Document Type: Article

References (77)

1. (a) Alexakis, A.; Mangeney, P.; Ghribi, A.; Marek, I.; Sedranu, R.; Guir, C.; Normant, J. Pure Appl. Chem. 1988, 60, 1.
2. (b) Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1990, 1, 477.
3. Denmark, S. E.; Marble, L. K. J. Org. Chem. 1990, 55, 1984.
4. Tamura, R.; Watabe, K. I.; Ono, N.; Yamamoto, Y. J. Org. Chem. 1992, 57, 4895.
5. Caló, V.; Fiandanese, V.; Nacci, A.; Scilimati, A. Tetrahedron 1994, 50, 7283.
6. (a) Harmata, M.; Claassen, R. J., II. Tetrahedron Lett. 1991, 32, 6497.
7. (b) Pyne, S. G.; Boche, G. Tetrahedron 1993, 49, 8449.
8. (c) Reggelin, M.; Weinberger, H. Tetrahedron Lett. 1992, 33, 6959.
9. Reggelin, M.; Weinberger, H. Angew. Chem. 1994, 106, 489;
10. Angew. Chem., Int. Ed. Engl. 1994, 33, 444.
11. (e) Gais, H.-J.; Müller, H.; Decker, J.; Hainz, R. Tetrahedron Lett. 1995, 36, 7437.
12. (f) Pyne, S. G.; Dong, Z.; Skelton, B. W.; White, A. H. J. Chem. Soc., Chem. Commun. 1994, 751.
13. Bund, J.; Gais, H.-J.; Erdelmeier, I. J. Am. Chem. Soc. 1991, 113, 1442.
14. Gais, H.-J.; Müller, H.; Bund, J.; Scommoda, M.; Brandt, J.; Raabe, G. J. Am. Chem. Soc. 1995, 117, 2453.
15. Johnson, C. R.; Zeller, J. R. Tetrahedron 1984, 40, 1225.
16. Erdelmeier, I; Gais, H.-J.; Lindner, H. J. Angew. Chem. 1986, 98, 912; Angew. Chem., Int. Ed. Engl. 1986, 25, 935.
17. Erdelmeier, I; Gais, H.-J.; Lindner, H. J. Angew. Chem. 1986, 98, 912; Angew. Chem., Int. Ed. Engl. 1986, 25, 935.
18. Pyne, S. G. J. Org. Chem. 1986, 51, 81.
19. Craig, D.; Geach, N. J. Synlett 1993, 481.
20. (a) Johnson, C. R.; Schroeck, C. W.; Shanklin, J. R. J. Am. Chem. Soc. 1973, 95, 7424.
21. (b) Johnson, C. R.; Jonsson, E. U.; Wambsgans, A. J. Org. Chem. 1919, 44, 2061.
22. Shiner, C. S.; Berks, A. H. J. Org. Chem. 1988, 53, 5542.
23. Reaction of sulfonimidates with (E/Z)-crotylmagnesium bromide gave nearly exclusively the corresponding (E) allylic sulfoximine; see ref 5c.
24. Gais, H. J.; Erdelmeier, I.; Lindner, H. J. Angew. Chem. 1986, 98, 914; Angew. Chem., Int. Ed. Engl. 1986, 25, 938.
25. Gais, H. J.; Erdelmeier, I.; Lindner, H. J. Angew. Chem. 1986, 98, 914; Angew. Chem., Int. Ed. Engl. 1986, 25, 938.
26. For similar observations, see ref 8.
27. Scommoda, M. Ph.D. Thesis, RWTH Aachen, 1995.
28. Imamoto, T.; Takiyama, N.; Nakamura, K.; Hatajima, T.; Kamiya, Y. J. Am. Chem. Soc. 1989, 111, 4392.
29. Gais, H.-J.; Scommoda, M.; Lenz, D. Tetrahedron Lett. 1994, 35, 7361.
30. (a) Hwang, K.-J.; Logusch, E. W.; Brannigan, L. H.; Thompson, M. R. J. Org. Chem. 1987, 52, 3435.
31. (b) Pyne, S. G.; Dikic, B. Tetrahedron Lett. 1990, 31, 5231.
32. (a) Johnson, C. R. In Comprehensive Organic Chemistry; Barton, D., Ollis, W. D., Eds.; Pergamon Press: Oxford, 1979; Vol. 1, p 223.
33. (b) Johnson, C. R. Aldrichim. Acta 1985, 18, 3.
34. Johnson, C. R.; Lavergne, O. M. J. Org. Chem. 1993, 58, 1922.
35. The four-membered cyclic allylic N-methyl-S-phenylsulfoximine is an exception of this rule; see ref 7.
36. For a quantitative palladium-catalyzed rearrangement of allylic N-tosylsulfoximines to the corresponding allylic sulfinamides, see: Pyne, S. G.; Dong, Z. Tetrahedron Lett. 1995, 36, 3029.
37. Gais, H.-J.; Lenz, D.; Raabe, G. Tetrahedron Lett. 1995, 36, 7437.
38. (a) Gais, H.-J.; Schmitz, E.; Raabe, G. Unpublished results.
39. (b) Gais, H.-J.; Pommerenke, A.; Raabe, G. Unpublished results.
40. (c) The authors have deposited atomic coordinates for 14 with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge. CB2 1EZ, UK.
41. (a) Dong, Z.; Pyne, S. G.; Skelton, B. W.; White, A. H. Aust. J. Chem. 1993, 46, 143.
42. Gais, H.-J.; Giesen, A.; Raabe, G. Unpublished results.
43. Kauffman, G. B.; Teter, L. A. Inorg. Synth. 1963, 7, 10.
44. (a) Jacques, J.; Gros C.; Bourcier, S. In Stereochemistry, Fundamentals and Methods, Absolute Configurations of 6000 Selected Compounds with One Asymmetric Carbon Atom; Kagan, H. B., Ed.; Georg Thieme Verlag: Stuttgart, 1977.
45. (b) Mislow, K.; Hamermesh, C. L. J. Am. Chem. Soc. 1955, 77, 1590.
46. (a) Meyers, A. I.; Williams, D. R. J. Org. Chem. 1978, 43, 3245.
47. (b) Meyers, A. I.; Williams, D. R.; White, S.; Erickson, G. W. J. Am. Chem. Soc. 1981, 103, 3088.
48. Takeuchi, S.; Miyoshi, N.; Ohgo, Y. Chem. Lett. 1992, 551.
49. Smolinsky, G.; Feuer, B. I. J. Am. Chem. Soc. 1964, 86, 3085.
50. (a) Bartlett, P. D.; Stauffer, C. H. J. Am. Chem. Soc. 1935, 57, 2580.
51. (b) Lardicci, L. L.; Salvadori, P.; Botteghi, C.; Pino, P. J. Chem. Soc., Chem. Commun. 1968, 381.
52. Enders, D.; Eichenauer, H. Angew. Chem. 1979, 91, 425; Angew. Chem., Int. Ed. Engl. 1979, 18, 397.
53. Enders, D.; Eichenauer, H. Angew. Chem. 1979, 91, 425; Angew. Chem., Int. Ed. Engl. 1979, 18, 397.
54. Ozonolysis of alkene 33 under the conditions described gave the corresponding dimethyl acetal instead of the aldehyde.
55. (a) Goering, H. L.; Kantner, S. S. J. Org. Chem. 1981, 46, 2144.
56. (b) Goering, H. L.; Kantner, S. S. J. Org. Chem. 1983, 48, 721.
57. (c) Tseng, C. C. T.; Paisley, S. D.; Goering, H. L. J. Org. Chem. 1986, 51, 2884.
58. (d) Underiner, T. L.; Paisley, S. D.; Schmitter, J.; Lesheski, L.; Goering, H. L. J. Org. Chem. 1989, 54, 2369.
59. (e) Underiner, T. L.; Goering, H. L. J. Org. Chem. 1990, 55, 2757.
60. (f) Bäckvall, J.-E.; Sellén, M.; Grant, B. J. Am. Chem. Soc. 1990, 112, 6615.
61. (g) Nakanishi, N.; Matsubara, S.; Utimoto, K.; Kozima, S.; Yamaguchi, R. J. Org. Chem. 1991, 56, 3278.
62. (h) Bäckvall, J.-E.; Persson, E. S. M.; Bombrun, A. J. Org. Chem. 1994, 59, 4126.
63. (i) Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135.
64. (j) Lipshutz, B. H. In Organometallics in Synthesis; Schlosser, M., Ed.; Wiley: New York, 1994; p 283.
65. NMR spectroscopic studies of [(trimethylsilyl)methyl]copper in the presence of lithium iodide gave evidence for the formation of a heterocuprate: Gais, H.-J.; Brandt, J. Unpublished results.
66. NMR spectroscopic studies of N-methylsulfoximines in the presence of boron trifluoride gave evidence for the formation of a complex: Gais, H.-J.; Pommerenke, A.; Bund, J; Müller, H. Unpublished results.
67. Pommerenke, A. Diploma Thesis, RWTH Aachen, 1994.
68. (a) Willert-Porada, M. A.; Burton, D. J.; Baenzinger, N. C. J. Chem. Soc., Chem. Commun. 1989, 1633.
69. (b) Power, P. P. Prog. Inorg. Chem. 1991, 39, 75.
70. (c) de la Pradilla, R. F.; Rubio, N. B.; Marino, J. P.; Viso, A. Tetrahedron Lett. 1992, 33, 4985.
71. Naumann, D.; Roy, T.; Tebbe, K.-F.; Crump, W. Angew. Chem. 1993, 105, 1555;
72. Angew. Chem., Int. Ed. Engl. 1993, 32, 1482.
73. (e) Snyder, J. P. Angew. Chem. 1995, 107, 112; Angew. Chem., Int. Ed. Engl. 1995, 34, 80.
74. (e) Snyder, J. P. Angew. Chem. 1995, 107, 112; Angew. Chem., Int. Ed. Engl. 1995, 34, 80.
75. (f) Dorigo, A. E.; Wanner, J.; Schleyer, P. v. R. Angew. Chem. 1995, 107, 492; Angew. Chem., Int. Ed. Engl. 1995, 34, 476.
76. (f) Dorigo, A. E.; Wanner, J.; Schleyer, P. v. R. Angew. Chem. 1995, 107, 492; Angew. Chem., Int. Ed. Engl. 1995, 34, 476.
77. For a proposal regarding the structure of π-alkene complexes of type C, see: Corey, E. J.; Boaz, N. W. Tetrahedron Lett. 1984, 29, 3063.