Preparation of functionalized dialkylzincs via a boron-zinc exchange. Reactivity and catalytic asymmetric addition to aldehydes

Journal of Organic Chemistry

Volumn 61, Issue 23, 1996, Pages 8229-8243

  Langer, Falk ^a   Schwink, Lothar ^a   Devasagayaraj, Arokiasamy ^a   Chavant, Pierre Yves ^a   Knochel, Paul ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000929712     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961129n     Document Type: Article

References (82)

1. (1)(a) Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117.
2. (b) Knochel, P. Synlett 1995, 393.
3. (c) Knochel, P. Chemtracts-Org. Chem. 1995, 8, 205.
4. (a) Knochel, P.; Yeh, M. C. P.; Berk, S. C.; Talbert, J. J. Org. Chem. 1988, 53, 2390.
5. (b) Knochel, P.; Rozema, M. J.; Tucker, C. E.; Retherford, C.; Furlong, M.; AchyuthaRao, S. Pure Appl. Chem. 1992, 64, 361.
6. Gaudemar, M. Bull. Soc. Chim. Fr. 1962, 974.
7. (a) Rieke, R. D. Science 1989, 246, 1260.
8. (b) Zhu, L.; Wehmeyer, R. M.; Rieke, R. D. J. Org. Chem. 1991, 56, 1445.
9. (a) Rozema, M. J.; AchyuthaRao, S.; Knochel, P. J. Org. Chem. 1992, 57, 1956.
10. (b) Knochel, P.; Vettel, S.; Eisenberg, C. Appl. Organomet. Chem. 1995, 9, 175.
11. (c) Devasagayaraj, A.; Schwink, L.; Knochel, P. J. Org. Chem. 1995, 60, 3311.
12. Rozema, M. J.; Eisenberg, C.; Lütjens, H., Ostwald, R.; Belyk, K.; Knochel, P. Tetrahedron Lett. 1993, 34, 3115.
13. (a) Langer, F.; Waas, J.; Knochel, P. Tetrahedron Lett. 1993, 34, 5261.
14. (b) Langer, F.; Devasagayaraj, A.; Chavant, P.-Y.; Knochel, P. Synlett 1994, 410.
15. Köster, R.; Griasnow, G.; Larbig, W.; Binger, P. Liebigs Ann. Chem. 1964, 672, 1.
16. Zakharkin, L. I.; Okhlobystin, O. Y. Z. Obsc. Khim. 1960, 30, 2134 (in English, 1960, 2109), Chem. Abstr. 1961, 55, 9319a.
17. Zakharkin, L. I.; Okhlobystin, O. Y. Z. Obsc. Khim. 1960, 30, 2134 (in English, 1960, 2109), Chem. Abstr. 1961, 55, 9319a.
18. Zakharkin, L. I.; Okhlobystin, O. Y. Z. Obsc. Khim. 1960, 30, 2134 (in English, 1960, 2109), Chem. Abstr. 1961, 55, 9319a.
19. Thiele, K.-H.; Engelhardt, G.; Köhler, J.; Arnstedt, M. J. Organomet. Chem. 1967, 9, 385.
20. (a) Oppolzer, W.; Radinov, R. N. Helv. Chim. Acta 1992, 75, 170.
21. (b) Srebnik, M. Tetrahedron Lett. 1991, 32, 2449.
22. (c) Oppolzer, W.; Radinov, R. N. Tetrahedron Lett. 1988, 29, 5645.
23. (a) Oppolzer, W.; Radinov, R. N. J. Am. Chem. Soc. 1993, 115, 1593.
24. (b) Oppolzer, W.; Radinov, R. N.; de Brabander, J. Tetrahedron Lett. 1995, 36, 2607.
25. Köster, R.; Binger, P. Inorg. Synth. 1974, 15, 141.
26. Brown, H. C. Organic Synthesis via Boranes; Wiley: New York, 1975.
27. (a) Duddu, R.; Eckhardt, M.; Furlong, M.; Knoess, H. P.; Berger, S.; Knochel, P. Tetrahedron 1994, 50, 2415.
28. (b) Wang, F.; Tang, J.; Labaudiniere, L.; Marek, I.; Normant, J. F. Synlett 1995, 723.
29. Knoess, H. P.; Furlong, M. T.; Rozema, M. J.; Knochel, P. J. Org. Chem. 1991, 56, 5974.
30. Villieras, J.; Rambaud, M. Synthesis 1982, 924.
31. Jubert, C.; Knochel, P. J. Org. Chem. 1992, 57, 5431.
32. (a) For excellent reviews, see: Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833.
33. (b) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49.
34. (a) Galsbol, F.; Steenbol, P.; Sondergaard-Sorensen, B. Acta Chem. Scand. 1972, 26, 3605.
35. (b) Larrow, J. F.; Jacobsen, E. N.; Gao, Y.; Hong, Y.; Nie, X.; Zepp, C. M. J. Org. Chem. 1994, 59, 1939.
36. (a) Takahashi, H.; Kawakita, T.; Ohno, M.; Yoshioka, M.; Kobayashi, S. Tetrahedron 1992, 48, 5691.
37. For other titanium-mediated asymmetric additions to aldehydes, see: (b) Schmidt, B.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1991, 30, 99. (c) Seebach, D.; Behrendt, L.; Felix, D. Angew. Chem., Int. Ed. Engl. 1991, 30, 1008. (d) Schmidt, B.; Seebach, D. Angew. Chem., Int. Ed. Engt. 1991, 30, 1321. (e) v. d. Bussche-Hünnefeld, J. L.; Seebach, D. Tetrahedron 1992, 48, 5719. (f) Seebach, D.; Plattner, D. A.; Beck, A. K.; Wang, Y. M.; Hunziker, D.; Petter, W. Helv. Chim. Acta 1992, 75, 2171. (g) Seebach, D.; Beck, A. K.; Schmidt, B.; Wang, Y. M. Tetrahedron 1994, 50, 4363. (h) Weber, B.; Seebach, D. Tetrahedron 1994, 50, 7473.
38. For other titanium-mediated asymmetric additions to aldehydes, see: (b) Schmidt, B.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1991, 30, 99. (c) Seebach, D.; Behrendt, L.; Felix, D. Angew. Chem., Int. Ed. Engl. 1991, 30, 1008. (d) Schmidt, B.; Seebach, D. Angew. Chem., Int. Ed. Engt. 1991, 30, 1321. (e) v. d. Bussche-Hünnefeld, J. L.; Seebach, D. Tetrahedron 1992, 48, 5719. (f) Seebach, D.; Plattner, D. A.; Beck, A. K.; Wang, Y. M.; Hunziker, D.; Petter, W. Helv. Chim. Acta 1992, 75, 2171. (g) Seebach, D.; Beck, A. K.; Schmidt, B.; Wang, Y. M. Tetrahedron 1994, 50, 4363. (h) Weber, B.; Seebach, D. Tetrahedron 1994, 50, 7473.
39. For other titanium-mediated asymmetric additions to aldehydes, see: (b) Schmidt, B.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1991, 30, 99. (c) Seebach, D.; Behrendt, L.; Felix, D. Angew. Chem., Int. Ed. Engl. 1991, 30, 1008. (d) Schmidt, B.; Seebach, D. Angew. Chem., Int. Ed. Engt. 1991, 30, 1321. (e) v. d. Bussche-Hünnefeld, J. L.; Seebach, D. Tetrahedron 1992, 48, 5719. (f) Seebach, D.; Plattner, D. A.; Beck, A. K.; Wang, Y. M.; Hunziker, D.; Petter, W. Helv. Chim. Acta 1992, 75, 2171. (g) Seebach, D.; Beck, A. K.; Schmidt, B.; Wang, Y. M. Tetrahedron 1994, 50, 4363. (h) Weber, B.; Seebach, D. Tetrahedron 1994, 50, 7473.
40. For other titanium-mediated asymmetric additions to aldehydes, see: (b) Schmidt, B.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1991, 30, 99. (c) Seebach, D.; Behrendt, L.; Felix, D. Angew. Chem., Int. Ed. Engl. 1991, 30, 1008. (d) Schmidt, B.; Seebach, D. Angew. Chem., Int. Ed. Engt. 1991, 30, 1321. (e) v. d. Bussche-Hünnefeld, J. L.; Seebach, D. Tetrahedron 1992, 48, 5719. (f) Seebach, D.; Plattner, D. A.; Beck, A. K.; Wang, Y. M.; Hunziker, D.; Petter, W. Helv. Chim. Acta 1992, 75, 2171. (g) Seebach, D.; Beck, A. K.; Schmidt, B.; Wang, Y. M. Tetrahedron 1994, 50, 4363. (h) Weber, B.; Seebach, D. Tetrahedron 1994, 50, 7473.
41. For other titanium-mediated asymmetric additions to aldehydes, see: (b) Schmidt, B.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1991, 30, 99. (c) Seebach, D.; Behrendt, L.; Felix, D. Angew. Chem., Int. Ed. Engl. 1991, 30, 1008. (d) Schmidt, B.; Seebach, D. Angew. Chem., Int. Ed. Engt. 1991, 30, 1321. (e) v. d. Bussche-Hünnefeld, J. L.; Seebach, D. Tetrahedron 1992, 48, 5719. (f) Seebach, D.; Plattner, D. A.; Beck, A. K.; Wang, Y. M.; Hunziker, D.; Petter, W. Helv. Chim. Acta 1992, 75, 2171. (g) Seebach, D.; Beck, A. K.; Schmidt, B.; Wang, Y. M. Tetrahedron 1994, 50, 4363. (h) Weber, B.; Seebach, D. Tetrahedron 1994, 50, 7473.
42. For other titanium-mediated asymmetric additions to aldehydes, see: (b) Schmidt, B.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1991, 30, 99. (c) Seebach, D.; Behrendt, L.; Felix, D. Angew. Chem., Int. Ed. Engl. 1991, 30, 1008. (d) Schmidt, B.; Seebach, D. Angew. Chem., Int. Ed. Engt. 1991, 30, 1321. (e) v. d. Bussche-Hünnefeld, J. L.; Seebach, D. Tetrahedron 1992, 48, 5719. (f) Seebach, D.; Plattner, D. A.; Beck, A. K.; Wang, Y. M.; Hunziker, D.; Petter, W. Helv. Chim. Acta 1992, 75, 2171. (g) Seebach, D.; Beck, A. K.; Schmidt, B.; Wang, Y. M. Tetrahedron 1994, 50, 4363. (h) Weber, B.; Seebach, D. Tetrahedron 1994, 50, 7473.
43. For other titanium-mediated asymmetric additions to aldehydes, see: (b) Schmidt, B.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1991, 30, 99. (c) Seebach, D.; Behrendt, L.; Felix, D. Angew. Chem., Int. Ed. Engl. 1991, 30, 1008. (d) Schmidt, B.; Seebach, D. Angew. Chem., Int. Ed. Engt. 1991, 30, 1321. (e) v. d. Bussche-Hünnefeld, J. L.; Seebach, D. Tetrahedron 1992, 48, 5719. (f) Seebach, D.; Plattner, D. A.; Beck, A. K.; Wang, Y. M.; Hunziker, D.; Petter, W. Helv. Chim. Acta 1992, 75, 2171. (g) Seebach, D.; Beck, A. K.; Schmidt, B.; Wang, Y. M. Tetrahedron 1994, 50, 4363. (h) Weber, B.; Seebach, D. Tetrahedron 1994, 50, 7473.
44. Schwink, L.; Knochel, P. Tetrahedron Lett. 1994, 35, 9007.
45. Rücker, C. Chem. Rev. 1995, 95, 1009.
46. Furhop, J.-H.; Bedurke, T.; Hahn, A.; Grund, S.; Gatzmann, J.; Riederer, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 350.
47. (a) Corey, E. J.; Suggs, J. W. Tetrahedron Lett. 1975, 2647.
48. (b) Pianeatelli, G.; Scettri, A.; D'Auria, M. Synthesis 1982, 245.
49. Parker, D. J. Chem. Soc., Perkin Trans. 2 1983, 83.
50. (a) Lipshutz, B. H. Synthesis 1987, 325.
51. (b) Lipshutz, B. H. Synlett 1990, 119.
52. (c) Lipshutz, B. H.; Wilhelm, R. S.; Kozlowski, J. A. Tetrahedron 1984, 40, 5005.
53. Piers, E.; Nagakura, I. Synth. Commun. 1975, 5, 193.
54. (a) Cunico, R. F.; Bedell, L. J. Org. Chem. 1980, 45, 4797.
55. (b) Cunico, R. F.; Dexheimer, E. M. Synth. React. Inorg. Met.-Org. Chem. 1974, 4, 23.
56. (c) Colvin, E. W. Silicon Reagents in Organic Synthesis; Academic Press: London, 1988; p 120.
57. (a) Bradley, D. C.; Thomas, I. M. J. Chem. Soc. 1959, 3404.
58. (b) Rust, J. B.; Takimoto, H. H.; Denault, G. C. J. Org. Chem. 1960, 25, 2040.
59. (c) Nowotny, S.; Vettel, S.; Knochel, P. Tetrahedron Lett. 1994, 35, 4539.
60. (a) Achyutha Rao, S.; Knochel, P. J. Am. Chem. Soc. 1991, 113, 5735.
61. (b) Chou, S.-S. P.; Kuo, H.-L.; Wang, C.-Y.; Tsai, C.-Y.; Sun, C.-M. J. Org. Chem. 1989, 54, 868.
62. (c) Shibata, K.; Aida, T.; Inoue, S. Tetrahedron Lett. 1992, 33, 1077.
63. Tucker, C. E.; Davidson, J.; Knochel, P. J. Org. Chem. 1992, 57, 3482.
64. Andersen, S. H.; Das, N. B.; Joergensen, R. D.; Kjeldsen, G.; Knudsen, J. S.; Subhash, S. C.; Torssell, K. B. G. Acta Chem. Scand. Ser. B 1982, 36, 1.
65. (a) Gaylord, N. G.; Eirich, F. R. J. Am. Chem. Soc. 1952, 74, 334.
66. (b) Zamarlik, M. H. C. R. Acad. Sci. (C) 1970, 271, 1138.
67. Deming, T. J.; Novak, B. M. J. Am. Chem. Soc. 1993, 115, 9101.
68. Antczak, K.; Kingston, J. F.; Alward, S. J.; Fallis. A. G. Can. J. Chem. 1984, 62, 829.
69. Lipshutz, B. H.; Parker, D. A.; Nguyen, S. L.; McCarthy, K. E.; Barton, J. C.; Whitney, S. E.; Kotsuni, H. Tetrahedron 1986, 42, 2873.
70. Barlin, G. B.; Ireland, S. J.; Jiravinyu, C.; Nguyen, T. M. T.; Kotecka, B.; Rieckmann, K. H. Aust. J. Chem. 1993, 46, 1695.
71. (a) Aleksandrowicz, P.; Piotrowska, H.; Sas, W. Tetrahedron 1982, 38, 1321.
72. (b) Ono, N.; Zinsmeister, K.; Kaji, A. Bull. Chem. Soc. Jpn. 1985, 58, 1069.
73. (a) Pirrung, M. C.; Webster, N. J. G. J. Org. Chem. 1987, 52, 3603.
74. (b) Corey, E. J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190.
75. Ashby, M. T.; Enemark, J. M.; Lichtenberger, D. L. Inorg. Chem. 1988, 27, 191.
76. Pettit, G. R.; Gupta, S. K. J. Chem. Soc., C 1986, 1208.
77. Salomon, R. G.; Coughlin, D. J.; Ghosh, S.; Zagorski, M. G. J. Am. Chem. Soc. 1982, 104, 998.
78. Kondo, T.; Akazome, M.; Tsuji, Y.; Watanabe, Y. J. Org. Chem. 1990, 55, 1286.
79. (a) Dominguez, X. A.; Barragan, V. J. Org. Chem. 1965, 30, 2049.
80. (b) Dave, P.; Byun, H.-S.; Engel, R. Synth. Commun. 1986, 16, 1343.
81. (a) Bentley, H. R.; Henry, J. A.; Irvine, D. S.; Mukerji, D.; Spring, F. S. J. Chem. Soc. 1955, 596.
82. (b) Beckmann, S.; Schtühle, H. Z. Naturforsch. 1968, 23b, 471.