Unique reactivities of new highly coordinated ate complexes of organozinc derivatives

Journal of the American Chemical Society

Volumn 118, Issue 36, 1996, Pages 8733-8734

  Uchiyama, Masanobu ^a   Koike, Minako ^a   Kameda, Mitsuyoshi ^a   Kondo, Yoshinori ^a   Sakamoto, Takao ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANOL; ZINC COMPLEX;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; TECHNIQUE;

EID: 0029842464     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961320e     Document Type: Article

References (31)

1. (a) Knochel, P.: Singer. R. D. Chem. Rev. 1993, 93. 2117-2188.
2. (b) Erdik. E. Tetrahedron 1987,43, 2203-2212.
3. (c) Erdik, E. Tetrahedron 1992, 48, 9577-9648.
4. (d) Knochel. P. In Comprehensive Organic Synthesis; Trost. B. M., Fleming, I., Eds.; Pergamon Press: Oxford. 1991 ; Vol. 1.pp. 211-229.
5. (a) Isobe. M.; Kondo, S.; Nagasawa, N.; Goto, T. Chem. Lett. 1977, 679-682.
6. (b) Tuckmantel, W.; Oshima, K.; Nozaki, H. Chem. Ber. 1986, 119, 1581-1593.
7. (c) Jansen, J. F. G. A.; Feringa, B. L. Tetrahedron Lett. 1988, 29. 3593-3596.
8. (d) Kjonaas, R. A.; Hoffer, R. K. J. Org. Chem. 1988. 53, 4133-4135.
9. (a) Kondo, Y.; Takazawa, N.; Yamazaki, C.; Sakamoto, T. J. Org. Chem. 1994, 59, 4717-4718.
10. (b) Harada, T.; Katsuhira, K.; Hattori. K.; Oku, A. J. Org. Chem. 1993, 58. 2958-2965.
11. (c) Harada, T.; Katsuhira, K.; Hara, D.; Kotani, Y.; Maejima, K.: Kaji. R.; Oku, A. J. Org. Chem. 1993. 58, 4897-4907.
12. (a) Hurd, D. T. J. Org. Chem. 1948, 13, 711-713;
13. (b) Nast, R. Angew. Chem. 1960, 72, 26-31.
14. (c) Seitz, L. M.; Brown, T. L. J. Am. Chem. Soc. 1966, 88. 4140-4147.
15. (d) Toppet, S.; Slinckx, G.; Smets, G. J. Organomet. Chem. 1967, 9, 205-213.
16. (e) Kaufmann, F.; Geraudelle, A.; Kaempf, B.; Schue, F.; Deluzarche, A.; Maillard, A. J. Organomet. Chem. 1974, 71, 11-15.
17. (f) Chastrette, M.; Gauthier, R. J. Organomet. Chem. 1974, 71, 11-15.
18. (a) Weiss, E.; Wolfrum, R. Chem. Ber. 1968, 101. 35-40.
19. (b) Weiss, E.; Plass, H. J. Organomet. Chem. 1968, 14, 21-31.
20. 3SiNCS (0.40 ppm).
21. 2, see: Hoskins. B. F.; Robson, R. J. Am. Chem. Soc. 1990, 112. 1546-1554.
22. Smith. J. G. Synthesis 1984, 629-656.
23. We recently reported a regioselective ring-opening reaction of epoxyorganometallic compounds which derived from halogen - metal exchange reaction using ate complexes. Kondo, Y.; Matsudaira, T.; Sato, J.; Murata, N.; Sakamoto, T. Angew. Chem., Int. Ed. Engl. 1996. 35, 736-738.
24. (a) Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135-631.
25. (b) Lipshutz, B. H.; Wilhelm, R. S.; Kozlowski, J. A. Tetrahedron 1984, 40, 5005-5038.
26. (c) Lipshutz, B. H. Synthesis 1987, 325-341.
27. (a) Snyder, J. P.; Spangler, D.D.; Behling, J. R. J. Org. Chem. 1994, 59, 2665-2667.
28. (b) Lipshutz, B. H.; Ellsworth, E. L.; Siahaan, T. J. J. Am. Chem. Soc. 1988, 110, 4834-4835.
29. (c) Bertz, B. H. J. Am. Chem. Soc. 1990, 112. 4031-4032.
30. (d) Lipshutz, B. H.; Sharma, S.: Ellsworth, E. J. Am. Chem. Soc. 1990, 112. 4032-4034.
31. Stemmler, T. L; Barnhart, T. M.; Penner-Hahn, J. E.; Tucker, C. E.; Knochel, P.; Boehme, M.; Frenking, G. J. Am. Chem. Soc. 1995, 117, 12489-12497.