Stereoselective Reactions Mediated by Functionalized Diorganozincs

Synlett

Volumn 1995, Issue 5, 1995, Pages 393-403

  Knochel, Paul ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

1,3 dimetallic compounds; asymmetric synthesis of secondary alcohols; functionalized organozinc reagents; hydronickelation; hydrozincation; palladium catalyzed radical cyclization

Indexed keywords

EID: 0003170224     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-1995-4997     Document Type: Article

References (96)

1. Grignard, V. C. R. Acad. Sc. Paris 1900, 130, 1322.
2. Ziegler, K.; Colonius, H. Liebigs Ann. Chem. 1930, 479, 135.
3. Wittig, G.; Pockels, U.; Droge, H. Chem. Ber. 1938, 71, 1903.
4. Gilman, H.; Langham, W.; Jacoby, A. L. J. Am. Chem. Soc. 1939, 61, 106.
5. (a) Posner, G. H. Org. React. 1972, 19, 1.
6. (b) Posner, G. H. Org. React. 1975, 22, 253.
7. (c) Lipshutz, B. H. Synthesis, 1987, 325.
8. (d) Lipshutz, B. H. Synlett 1990, 119.
9. (e) Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135.
10. (e) Normant, J. F.; Alexakis, A. Synthesis 1981, 841.
11. (a) Weidmann, B.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1983, 22, 31.
12. (b) Reetz, M. T. Top. Curr. Chem. 1982, 106, 1.
13. (c) Reetz, M. T. Organometallics in Synthesis - A Manual Ed. Schlosser, M. John Wiley, New York, 1994, p. 198.
14. (a) Cahiez, G. Actual. Chim. 1984 (Sept), 24.
15. 3(b) Cahiez, G.; Laboue, B. Tetrahedron Lett. 1989, 30, 3545.
16. (c) Cahiez, G.; Laboue, B. Tetrahedron Lett. 1989, 30, 7369.
17. (d) Cahiez, G.; Alami, M. Tetrahedron 1989, 45, 4163.
18. (e) Cahiez, G.; Chavant, P.-Y.; Metais, E. Tetrahedron Lett. 1992, 33, 5245.
19. Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117.
20. Hunsdiecker, H.; Erlbach, H.; Vogt, E. German Patent 722467, 1942;
21. Chem. Abstr. 1943, 37, P5080.
22. (a) Tamaru, Y.; Ochiai, H.; Nakamura, T.; Yoshida, Z. Tetrahedron Lett. 1986, 27, 955.
23. (b) Tamaru, Y.; Ochiai, H.; Nakamura, T.; Yoshida, Z. Angew. Chem. 1987, 99, 1193.
24. (c) Tamaru, Y. New Trends in Organometallic Chemistry; Sakurai, H., Ed.; Tohoku University: Sendai, Japan, 1990; p. 304.
25. Knochel, P.; Yeh, M. C. P.; Berk, S. C.; Talbert. J. J. Org. Chem. 1988, 53, 2390.
26. (a) JanikaramRao, C.; Knochel, P. J. Org. Chem. 1991, 56, 4593.
27. (b) JanikaramRao, C.; Knochel, P. Tetrahedron 1993, 49, 29.
28. Knoess, H. P.; Furlong, M. T.; Rozema, M. J.; Knochel, P. Org. Chem. 1991, 56, 5974.
29. (a) Duddu, R.; Eckhardt, M.; Furlong, M.; Knoess, H. P.; Berger, S.; Knochel, P. Tetrahedron 1994, 50, 2415.
30. (b) Jackson, R. F. W.; Wishart, N.; Wood, A.; James, K.; Wythes, M. J. J. Org. Chem. 1992, 57, 3397.
31. (c) Dunn, M. J.; Jackson, R. F. W.; Pietruszka, J.; Wishart, N.; Ellis, D.; Wythes, M. J. Synlett 1993, 499.
32. (d) Dow, R. L.; Bechle, B. M. Synlett 1994, 293.
33. (e) Fraser, J. L.; Jackson, R. F. W.; Porter, B. Synlett 1994, 379.
34. Zhu, L.; Wehmeyer, R. M.; Rieke, R. D. J. Org. Chem. 1991, 56, 1445.
35. (a) Majid, T. N.; Knochel, P. Tetrahedron Lett. 1990, 31, 4413.
36. (b) Tucker, C. E.; Majid, T. N.; Knochel, P. J. Am. Chem. Soc. 1992, 114, 3983.
37. (c) Furstner, A.; Singer, R.; Knochel, P. Tetrahedron Lett. 1994, 35, 1047.
38. (a) Bailey, W. F.; Patricia, J. J. J. Organomet. Chem. 1988, 352, 1.
39. (b) Bailey, W. F.; Punzalan, E. R. J. Org. Chem. 1990, 55, 5404.
40. (c) Negishi, E.; Swanson, D. R.; Rousset, C. J. J. Org. Chem. 1990, 55, 5406.
41. Furukawa, J.; Kawabata, N. Adv. Organomet. Chem. 1974, 12, 83.
42. Rozema, M. J.; AchyuthaRao, S.; Knochel, P. J. Org. Chem. 1992, 57, 1956.
43. (a) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833.
44. (b) Duthaler, R. O.; Hafner, A. Chem. Rev. 1992, 92, 807.
45. (c) Evans, D. A. Science 1988, 240, 420.
46. (d) Noyori, R.; Kitamura, M. Angew. Chem. Int. Ed. Engl. 1991, 30, 49.
47. (a) Yoshioka, M.; Kawakita, T.; Ohno, M. Tetrahedron Lett. 1989, 30, 1657.
48. (b) Takahashi, H.; Kawakita, T.; Yoshioka, M. Kobayashi, S.; Ohno, M. Tetrahedron Lett. 1989, 30, 7095.
49. (c) Takahashi, H.; Kawakita, T.; Ohno, M.; Yoshioka, M.; Kobayashi, S. Tetrahedron 1992, 48, 5691.
50. Vettel, S.; Knochel, P. Tetrahedron Lett. 1994, 35, 5849.
51. Hayashi, T.; Konishi, M.; Kobori, Y.; Kumada, M.; Higuchi, T.; Hirotsu, K. J. Am. Chem. Soc. 1984, 106, 158.
52. Stadtmiiller, H.; Lentz, R.; Tucker, C. E.; Stiidemann, T.; Domer, W.; Knochel, P. J. Am. Chem. Soc. 1993, 115, 7027.
53. Amatore, C.; Jutand, A.; Suarez, A. J. Am. Chem. Soc. 1993, 115, 9531.
54. Chanon, M. Bull. Soc. Chim. France (II), 1982, 197.
55. Meyer, C.; Marek, I.; Courtemanche, G.; Normant, J.-F. Tetrahedron 1994, 50, 11665.
56. Stadtmiiller, H.; Tucker, C. E.; Vaupel, A.; Knochel, P. Tetrahedron Lett. 1993, 34, 7911.
57. (a) Beckwith, A. L. J. Tetrahedron 1981, 37, 3073.
58. (b) Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron 1985, 41, 3925.
59. (a) Giese, B. in Radicals in Organic Synthesis. Formation of Carbon-Carbon Bonds, Pergamon Press, Oxford, 1986;
60. (b) Motherwell, W. B.; Crich, D. in Free Radical Chain Reactions in Organic Synthesis, Academic Press, London, 1991.
61. RajanBabu, T. V.; Fukunaga, T. J. Am. Chem. Soc. 1989, 111, 296.
62. Vaupel, A.; Knochel, P. Tetrahedron Lett. 1994, 35, 8349.
63. Ostwald, R.; Chavant, P.-Y.; Stadtmiiller, H.; Knochel, P. J. Org. Chem. 1994, 59, 4143.
64. Vaupel, A.; Knochel, P. Tetrahedron Lett. 1995, 36, 231.
65. de Azevedo, M. B. M.; Murta, M. M.; Greene, A. E. J. Org. Chem. 1992, 57, 4567.
66. (a) Knochel, P.; Xiao, C.; Yeh, M. C. P. Tetrahedron Lett. 1988, 29, 6697.
67. (b) Knochel, P.; Yeh, M. C. P.; Xiao, C. Organometallics 1989, 8, 2831.
68. (a) Klement, I.; Liitjens, H.; Knochel, P. Tetrahedron Lett. 1995, 36, in press
69. (b) Klement, I.; Knochel, P. manuscript in preparation.
70. (a) Riess, J. G.; Le Blanc, M. Pure Appl. Chem. 1982, 54, 2383.
71. (b) Horvath, I. T.; Rabai, J. Science 1994, 266, 72.
72. Yeh, M. C. P.; Knochel, P. Tetrahedron Lett. 1989, 30, 4799.
73. Stadtmiiller, H.; Knochel, P. Synlett 1995, 463.
74. (a) Helmchen, G.; Goeke, A.; Lauer, G.; Urmann, M.; Fries, J. Angew. Chem. Int. Ed. Engl. 1990, 29, 1024.
75. (b) Kitahara, T.; Nishi, T.; Mori, K. Tetrahedron 1991, 47, 6999.
76. (c) Sarkar, T. K.; Ghorai, B. K.; Banetji, A. Tetrahedron Lett. 1994, 35, 6907.
77. (d) Busato, S.; Scheffold, R. Helv. Chim. Acta 1994, 77, 92.
78. Koster, R. Ed. Methoden der Organischen Chemie; Organobor-Verbindungen Vol. I-III, Thieme: Stuttgart, 1982.
79. (a) Zakharkin, L. I.; Okhlobystin, O. Y. Z. Obsc. Chim. 1960, 30, 2134 (in english, 1960, 2109);
80. Chem. Abstr. 1961, 55, 9319a.
81. (b) Thiele, K.-H.; Engelhardt, G.; Kohler, J.; Amstedt, M. J. Organomet. Chem. 1967, 9, 385.
82. Langer, F.; Devasagayaraj, A.; Chavant, P.-Y.; Knochel, P. Synlett 1994, 410.
83. Koster, R.; Griasnow, G.; Larbig, W.; Binger, P. Liebigs Ann. Chem. 1964, 672, 1.
84. Knoess, H. P.; Furlong, M. T.; Rozema, M. J.; Knochel, P. J. Org. Chem. 1991, 56, 5974.
85. Devasagayaraj, A.; Schwink, L.; Knochel, P. J. Org. Chem. 1995, 60, in press.
86. Fuhrhop, J.-H.; Bedurke, T.; Hahn, A.; Grand, S.; Gatzmann, J.; Riederer, M. Angew. Chem. 1994, 106, 351.
87. Schwink, L.; Knochel, P. Tetrahedron Lett. 1994, 35, 9007.
88. (a) Berk, S. C.; Knochel, P.; Yeh, M. C. P. J. Org. Chem. 1988, 53, 5789.
89. (b) Berk, S. C.; Yeh, M. C. P.; Jeong, N.; Knochel, P. Organometallics 1990, 9, 3053.
90. (a) Bickelhaupt, F. Angew. Chem. Int. Ed. Engl. 1987, 26, 990.
91. (b) Seetz, J. W. F. L.; Schat, G.; Akkerman, O. S.; Bickelhaupt, F. J. Am. Chem. Soc. 1982, 104, 6848.
92. (c) Seetz, J. W. F. L.; Hartog, F. A.; Bohm, H. P.; Blomberg, C.; Akkerman, O. S.; Bickelhaupt, F. Tetrahedron Lett. 1982, 23, 1497.
93. Eick, H.; Palmer, N.; Knochel, P. manuscript in preparation.
94. Vettel, S.; Vaupel, A.; Knochel, P. Tetrahedron Lett. 1995, 36, 1023.
95. Felkin, H.; Swierczewski, G. Tetrahedron 1975, 31, 2735.
96. Vaupel, A.; Stiidemann, T.; Knochel, P. manuscript in preparation.