An ab initio computational study on the reaction of organotin enolates: Comparison of highly coordinated tin reagent with noncoordinated reagent

Journal of the American Chemical Society

Volumn 122, Issue 31, 2000, Pages 7549-7555

  Yasuda, Makoto ^a   Chiba, Kouji ^b   Baba, Akio ^a  

^a OSAKA UNIVERSITY   (Japan)

^b Ryoka Systems Inc   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; BROMIDE; HALIDE; ORGANOTIN COMPOUND; OXYGEN; TIN;

ARTICLE; CALCULATION; CHEMICAL REACTION; CONTROLLED STUDY;

EID: 0034625923     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0003775     Document Type: Article

References (31)

1. Harrison, P. G. Chemistry of Tin; Blackie: Glasgow and London, 1989.
2. 3SnCl) was the first example of a highly coordinated tin compound. Hulme, R. J. Chem. Soc. 1963, 1524.
3. (a) Yasuda, M.; Hayashi, K.; Katoh, Y.; Shibata, I.; Baba, A. J. Am. Chem. Soc. 1998, 120, 715.
4. (b) Yasuda, M.; Oh-hata, T.; Shibata, I.; Baba, A.; Matsuda, H. J. Chem. Soc., Perkin Trans. 1 1993, 859.
5. (c) Yasuda, M.; Katoh, Y.; Shibata, I.; Baba, A.; Matsuda, H.; Sonoda, N. J. Org. Chem. 1994, 59, 4386.
6. (d) Yasuda, M.; Ohigashi, N.; Shibata, I.; Baba, A. J. Org. Chem. 1999, 64, 2180.
7. (a) Kawakami, T.; Shibata, I.; Baba, A. J. Org. Chem. 1996, 61, 82.
8. (b) Suwa, T.; Shibata, I.; Baba, A. Organometallics 1999, 18, 3965.
9. (a) Noltes, J. G.; Creemers, H. M. J. C.; Van Der Kerk, G. J. M. J. Organomet. Chem. 1968, 11, 21.
10. (b) Labadie, S. S.; Stille, J. K. Tetrahedron 1984, 40, 2329.
11. (c) Yamamoto, Y.; Yatagi, H.; Maruyama, K. J. Chem. Soc., Chem. Commun. 1981, 162.
12. A high temperatrue is required for halide-coupling with tin enolates. Odic, Y.; Pereyre, M. J. Organomet. Chem. 1973, 55, 273.
13. (a) Kuwajima, I.; Nakamura, E. J. Am. Chem. Soc. 1975, 97, 3257.
14. (b) Kuwajima, I.; Nakamura, E.; Shimizu, M. J. Am. Chem. Soc. 1982, 104, 1025.
15. (c) Kraus, G. A.; Roth, B.; Frazier, K.; Shimagaki, M. J. Am. Chem. Soc. 1982, 104, 1114.
16. (a) Nakamura, E.; Shimizu, M.; Kuwajima, I.; Sakata, J.; Yokoyama, K.; Noyori, R. J. Am. Chem. Soc. 1983, 48, 932.
17. (b) Noyori, R.; Nishida, I.; Sakata, J. J. Am. Chem. Soc. 1981, 103, 2106.
18. Roothaan, C. C. J. Rev. Mod. Phys. 1951, 23, 69.
19. Turbomole, ab initio Electronic Structure Program from MSI of San Diego.
20. NBO Version 3.1. Glendening, E. D.; Reed, A. E.; Carpenter, J. R.; Weinhold, F.
21. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Gaussian, Inc.: Pittsburgh, PA, 1998.
22. Schäfer, A.; Horn, H.; Ahlrichs, R. J. Chem. Phys. 1992, 97, 2571.
23. LaJohn, L. A.; Christiansen, P. A.; Ross, R. B. J. Chem. Phys. 1987, 87, 2812.
24. The optimized geometry of silyl enolate has been reported. Takahashi, M.; Kira, M. J. Am. Chem. Soc. 1999, 121, 8597.
25. (a) Holecek, J.; Nadvornik, M.; Handlir, K. J. Organomet. Chem. 1983, 241, 177.
26. (b) Nadvornik, M.; Holecek, J.; Handlir. K. J. Organomet. Chem. 1984, 275, 43.
27. Zimmerman, H. E.; Traxler, M. D. J. Am. Chem. Soc. 1957, 79, 1920.
28. The nucleophilicity and Lewis acidity of pentacoordinated allylsilicates have been discussed. Kira, M.; Sato, K.; Sakurai, H. J. Am. Chem. Soc. 1988, 110, 4599.
29. High coordination of trichlorosilyl or dimethylsilyl enolates accelerates the addition to aldehydes probably because metal centers still have enough Lewis acidity to accept carbonyl oxygen owing to electronic or steric reasons. In those cases, the increase of nucleophilicity would be much more important than the change of acidity. For example: (a) Denmark, S. E.; Winter, S. B. D.; Su, W. X.; Wong, K.-T. J. Am. Chem. Soc. 1996, 118. 7404. (b) Miura, K.; Sato, H.; Tamaki, K.; Ito, H.; Hosomi, A. Tetrahedron Lett. 1998, 39, 2585.
30. High coordination of trichlorosilyl or dimethylsilyl enolates accelerates the addition to aldehydes probably because metal centers still have enough Lewis acidity to accept carbonyl oxygen owing to electronic or steric reasons. In those cases, the increase of nucleophilicity would be much more important than the change of acidity. For example: (a) Denmark, S. E.; Winter, S. B. D.; Su, W. X.; Wong, K.-T. J. Am. Chem. Soc. 1996, 118. 7404. (b) Miura, K.; Sato, H.; Tamaki, K.; Ito, H.; Hosomi, A. Tetrahedron Lett. 1998, 39, 2585.
31. N2 type reaction course as shown in Figure 5 and Scheme 6.