Understanding the correlation of structure and selectivity in the chiral-phosphoramide-catalyzed enantioselective allylation reactions: Solution and solid-state structural studies of bisphosphoramide·SnCl4 complexes

Journal of the American Chemical Society

Volumn 125, Issue 8, 2003, Pages 2208-2216

  Denmark, Scott E ^a   Fu, Jiping ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLATION REACTIONS;

CHLORIDE MINERALS; COMPLEXATION; METHANE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SINGLE CRYSTALS; STEREOCHEMISTRY; TIN; X RAY CRYSTALLOGRAPHY;

PHOSPHORUS COMPOUNDS;

ALLYL COMPOUND; PHOSPHORAMIDIC ACID; STANNIC CHLORIDE;

ALLYLATION; ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; COMPLEX FORMATION; ENANTIOSELECTIVITY; STEREOCHEMISTRY; X RAY ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0037466984     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja021280g     Document Type: Article

References (50)

1. Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Heidelberg, 1999; Vols. I-III.
2. (a) Shambayati, S.; Crowe, W. E.; Schreiber, S. L. Angew. Chem., Int. Ed. Engl. 1990, 29, 256.
3. (b) Seebach, D. Angew. Chem., Int. Ed. Engl. 1988, 27, 1624.
4. (c) Seebach, D.; Beck, A. K.; Heckel, A. Angew. Chem., Int. Ed. 2001, 20, 92.
5. (d) Gaul, C.; Schweizer, B. W.; Seebach, D. Helv. Chim. Acta 2002, 85, 1546.
6. (e) Boche, G. Angew. Chem., Int. Ed. Engl. 1989, 28, 277.
7. (f) Ooi, T.; Maruoka, K. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000; Chapter 1.
8. (g) Saito, S.; Yamamoto, H. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000; Chapter 2.
9. General reference on the properties and the application of phosphoramides: (a) Normant, H. Russ. Chem. Rev. (Engl. Transl.) 1970, 39, 457. (b) Reichardt, C. Solvents and Solvent Effects in Organic Chemistry; VCH: Germany, 1988. (c) Luteri, G. F.; Ford, W. T. J. Org. Chem. 1977, 42, 820. (d) Gutmann, V. The Donor-Acceptor Approach to Molecular Interactions; Plenum: New York, 1978.
10. General reference on the properties and the application of phosphoramides: (a) Normant, H. Russ. Chem. Rev. (Engl. Transl.) 1970, 39, 457. (b) Reichardt, C. Solvents and Solvent Effects in Organic Chemistry; VCH: Germany, 1988. (c) Luteri, G. F.; Ford, W. T. J. Org. Chem. 1977, 42, 820. (d) Gutmann, V. The Donor-Acceptor Approach to Molecular Interactions; Plenum: New York, 1978.
11. General reference on the properties and the application of phosphoramides: (a) Normant, H. Russ. Chem. Rev. (Engl. Transl.) 1970, 39, 457. (b) Reichardt, C. Solvents and Solvent Effects in Organic Chemistry; VCH: Germany, 1988. (c) Luteri, G. F.; Ford, W. T. J. Org. Chem. 1977, 42, 820. (d) Gutmann, V. The Donor-Acceptor Approach to Molecular Interactions; Plenum: New York, 1978.
12. General reference on the properties and the application of phosphoramides: (a) Normant, H. Russ. Chem. Rev. (Engl. Transl.) 1970, 39, 457. (b) Reichardt, C. Solvents and Solvent Effects in Organic Chemistry; VCH: Germany, 1988. (c) Luteri, G. F.; Ford, W. T. J. Org. Chem. 1977, 42, 820. (d) Gutmann, V. The Donor-Acceptor Approach to Molecular Interactions; Plenum: New York, 1978.
13. Denmark, S. E.; Su, X.; Nishigaichi, Y.; Coe, D. M.; Wong, K.-T.; Winter, S. B. D.; Choi, J. Y. J. Org. Chem. 1999, 64, 1958.
14. Chiral Lewis base-catalyzed aldol reaction: Denmark, S. E.; Stavenger, R. A. Acc. Chem. Res. 2000, 33, 432.
15. (a) Chiral-phosphoramide-catalyzed allylation reaction: Denmark, S. E.; Coe, D. M.; Pratt, N. E.; Griedel, B. D. J. Org. Chem. 1994, 59, 6161.
16. (b) Denmark, S. E.; Fu, J. J. Am. Chem. Soc. 2000, 122, 12021.
17. (c) Denmark, S. E.; Fu, J. J. Am. Chem. Soc. 2001, 123, 9488.
18. (d) Denmark, S. E.; Fu, J. Org. Lett. 2002, 4, 1951.
19. (e) Denmark, S. E.; Fu, J. Chem. Commun. 2003, 167.
20. 4: Denmark, S. E.; Barsanti, P. A.; Wong, K.-T.; Stavenger, R. A. J. Org. Chem. 1998, 63, 2428.
21. (b) Denmark, S. E.; Wynn, T.; Jellerichs, B. G. Angew. Chem., Int. Ed. 2001, 40, 2255.
22. (c) Denmark, S. E.; Wynn, T. J. Am. Chem. Soc. 2001, 123, 6199.
23. (d) Denmark, S. E.; Wynn, T.; Beutner, G. L. J. Am. Chem. Soc. 2002, 124, 13405.
24. Reference on other chiral-Lewis-base-catalyzed enantioselective allylation reactions: (a) Iseki, K.; Kuroki, Y.; Takahashi, M.; Kobayashi, Y. Tetrahedron Lett. 1996, 37, 5149. (b) Iseki, K.; Kuroki, Y.; Takahashi, M.; Kishimoto, S.; Kobayashi, Y. Tetrahedron 1997, 53, 3513. (c) Hellwig, J.; Belser, T.; Muller, J. F. K. Tetrahedron Lett. 2001, 42, 5417. (d) Iseki, K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Tetrahedron Lett. 1998, 39, 2767. (e) Iseki, K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Tetrahedron 1999, 55, 977. (f) Nakajima, M.; Saito, M.; Shiro, M.; Hashimoto, S. J. Am. Chem. Soc. 1998, 120, 6419. (g) Malkov, A. V.; Orsini, M.; Pernazza, D.; Muir, K. W.; Langer, V.; Meghani, P.; Kocovsky, P. Org. Lett. 2002, 4, 1047. (h) Shimada, T.; Kina, A.; Ikeda, S.; Hayashi, T. Org. Lett. 2002, 4, 2799. (i) Chataigner, I.; Piarulli, U.; Gennari, C. Tetrahedron Lett. 1999, 40, 3633. (j) Angell, R. M.; Barrett, A. G. M.; Braddock, D. C.; Swallow, S.; Vickery, B. D. Chem. Commun. 1997, 919.
25. Reference on other chiral-Lewis-base-catalyzed enantioselective allylation reactions: (a) Iseki, K.; Kuroki, Y.; Takahashi, M.; Kobayashi, Y. Tetrahedron Lett. 1996, 37, 5149. (b) Iseki, K.; Kuroki, Y.; Takahashi, M.; Kishimoto, S.; Kobayashi, Y. Tetrahedron 1997, 53, 3513. (c) Hellwig, J.; Belser, T.; Muller, J. F. K. Tetrahedron Lett. 2001, 42, 5417. (d) Iseki, K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Tetrahedron Lett. 1998, 39, 2767. (e) Iseki, K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Tetrahedron 1999, 55, 977. (f) Nakajima, M.; Saito, M.; Shiro, M.; Hashimoto, S. J. Am. Chem. Soc. 1998, 120, 6419. (g) Malkov, A. V.; Orsini, M.; Pernazza, D.; Muir, K. W.; Langer, V.; Meghani, P.; Kocovsky, P. Org. Lett. 2002, 4, 1047. (h) Shimada, T.; Kina, A.; Ikeda, S.; Hayashi, T. Org. Lett. 2002, 4, 2799. (i) Chataigner, I.; Piarulli, U.; Gennari, C. Tetrahedron Lett. 1999, 40, 3633. (j) Angell, R. M.; Barrett, A. G. M.; Braddock, D. C.; Swallow, S.; Vickery, B. D. Chem. Commun. 1997, 919.
26. Reference on other chiral-Lewis-base-catalyzed enantioselective allylation reactions: (a) Iseki, K.; Kuroki, Y.; Takahashi, M.; Kobayashi, Y. Tetrahedron Lett. 1996, 37, 5149. (b) Iseki, K.; Kuroki, Y.; Takahashi, M.; Kishimoto, S.; Kobayashi, Y. Tetrahedron 1997, 53, 3513. (c) Hellwig, J.; Belser, T.; Muller, J. F. K. Tetrahedron Lett. 2001, 42, 5417. (d) Iseki, K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Tetrahedron Lett. 1998, 39, 2767. (e) Iseki, K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Tetrahedron 1999, 55, 977. (f) Nakajima, M.; Saito, M.; Shiro, M.; Hashimoto, S. J. Am. Chem. Soc. 1998, 120, 6419. (g) Malkov, A. V.; Orsini, M.; Pernazza, D.; Muir, K. W.; Langer, V.; Meghani, P.; Kocovsky, P. Org. Lett. 2002, 4, 1047. (h) Shimada, T.; Kina, A.; Ikeda, S.; Hayashi, T. Org. Lett. 2002, 4, 2799. (i) Chataigner, I.; Piarulli, U.; Gennari, C. Tetrahedron Lett. 1999, 40, 3633. (j) Angell, R. M.; Barrett, A. G. M.; Braddock, D. C.; Swallow, S.; Vickery, B. D. Chem. Commun. 1997, 919.
27. Reference on other chiral-Lewis-base-catalyzed enantioselective allylation reactions: (a) Iseki, K.; Kuroki, Y.; Takahashi, M.; Kobayashi, Y. Tetrahedron Lett. 1996, 37, 5149. (b) Iseki, K.; Kuroki, Y.; Takahashi, M.; Kishimoto, S.; Kobayashi, Y. Tetrahedron 1997, 53, 3513. (c) Hellwig, J.; Belser, T.; Muller, J. F. K. Tetrahedron Lett. 2001, 42, 5417. (d) Iseki, K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Tetrahedron Lett. 1998, 39, 2767. (e) Iseki, K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Tetrahedron 1999, 55, 977. (f) Nakajima, M.; Saito, M.; Shiro, M.; Hashimoto, S. J. Am. Chem. Soc. 1998, 120, 6419. (g) Malkov, A. V.; Orsini, M.; Pernazza, D.; Muir, K. W.; Langer, V.; Meghani, P.; Kocovsky, P. Org. Lett. 2002, 4, 1047. (h) Shimada, T.; Kina, A.; Ikeda, S.; Hayashi, T. Org. Lett. 2002, 4, 2799. (i) Chataigner, I.; Piarulli, U.; Gennari, C. Tetrahedron Lett. 1999, 40, 3633. (j) Angell, R. M.; Barrett, A. G. M.; Braddock, D. C.; Swallow, S.; Vickery, B. D. Chem. Commun. 1997, 919.
28. Reference on other chiral-Lewis-base-catalyzed enantioselective allylation reactions: (a) Iseki, K.; Kuroki, Y.; Takahashi, M.; Kobayashi, Y. Tetrahedron Lett. 1996, 37, 5149. (b) Iseki, K.; Kuroki, Y.; Takahashi, M.; Kishimoto, S.; Kobayashi, Y. Tetrahedron 1997, 53, 3513. (c) Hellwig, J.; Belser, T.; Muller, J. F. K. Tetrahedron Lett. 2001, 42, 5417. (d) Iseki, K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Tetrahedron Lett. 1998, 39, 2767. (e) Iseki, K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Tetrahedron 1999, 55, 977. (f) Nakajima, M.; Saito, M.; Shiro, M.; Hashimoto, S. J. Am. Chem. Soc. 1998, 120, 6419. (g) Malkov, A. V.; Orsini, M.; Pernazza, D.; Muir, K. W.; Langer, V.; Meghani, P.; Kocovsky, P. Org. Lett. 2002, 4, 1047. (h) Shimada, T.; Kina, A.; Ikeda, S.; Hayashi, T. Org. Lett. 2002, 4, 2799. (i) Chataigner, I.; Piarulli, U.; Gennari, C. Tetrahedron Lett. 1999, 40, 3633. (j) Angell, R. M.; Barrett, A. G. M.; Braddock, D. C.; Swallow, S.; Vickery, B. D. Chem. Commun. 1997, 919.
29. Reference on other chiral-Lewis-base-catalyzed enantioselective allylation reactions: (a) Iseki, K.; Kuroki, Y.; Takahashi, M.; Kobayashi, Y. Tetrahedron Lett. 1996, 37, 5149. (b) Iseki, K.; Kuroki, Y.; Takahashi, M.; Kishimoto, S.; Kobayashi, Y. Tetrahedron 1997, 53, 3513. (c) Hellwig, J.; Belser, T.; Muller, J. F. K. Tetrahedron Lett. 2001, 42, 5417. (d) Iseki, K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Tetrahedron Lett. 1998, 39, 2767. (e) Iseki, K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Tetrahedron 1999, 55, 977. (f) Nakajima, M.; Saito, M.; Shiro, M.; Hashimoto, S. J. Am. Chem. Soc. 1998, 120, 6419. (g) Malkov, A. V.; Orsini, M.; Pernazza, D.; Muir, K. W.; Langer, V.; Meghani, P.; Kocovsky, P. Org. Lett. 2002, 4, 1047. (h) Shimada, T.; Kina, A.; Ikeda, S.; Hayashi, T. Org. Lett. 2002, 4, 2799. (i) Chataigner, I.; Piarulli, U.; Gennari, C. Tetrahedron Lett. 1999, 40, 3633. (j) Angell, R. M.; Barrett, A. G. M.; Braddock, D. C.; Swallow, S.; Vickery, B. D. Chem. Commun. 1997, 919.
30. Reference on other chiral-Lewis-base-catalyzed enantioselective allylation reactions: (a) Iseki, K.; Kuroki, Y.; Takahashi, M.; Kobayashi, Y. Tetrahedron Lett. 1996, 37, 5149. (b) Iseki, K.; Kuroki, Y.; Takahashi, M.; Kishimoto, S.; Kobayashi, Y. Tetrahedron 1997, 53, 3513. (c) Hellwig, J.; Belser, T.; Muller, J. F. K. Tetrahedron Lett. 2001, 42, 5417. (d) Iseki, K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Tetrahedron Lett. 1998, 39, 2767. (e) Iseki, K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Tetrahedron 1999, 55, 977. (f) Nakajima, M.; Saito, M.; Shiro, M.; Hashimoto, S. J. Am. Chem. Soc. 1998, 120, 6419. (g) Malkov, A. V.; Orsini, M.; Pernazza, D.; Muir, K. W.; Langer, V.; Meghani, P.; Kocovsky, P. Org. Lett. 2002, 4, 1047. (h) Shimada, T.; Kina, A.; Ikeda, S.; Hayashi, T. Org. Lett. 2002, 4, 2799. (i) Chataigner, I.; Piarulli, U.; Gennari, C. Tetrahedron Lett. 1999, 40, 3633. (j) Angell, R. M.; Barrett, A. G. M.; Braddock, D. C.; Swallow, S.; Vickery, B. D. Chem. Commun. 1997, 919.
31. Reference on other chiral-Lewis-base-catalyzed enantioselective allylation reactions: (a) Iseki, K.; Kuroki, Y.; Takahashi, M.; Kobayashi, Y. Tetrahedron Lett. 1996, 37, 5149. (b) Iseki, K.; Kuroki, Y.; Takahashi, M.; Kishimoto, S.; Kobayashi, Y. Tetrahedron 1997, 53, 3513. (c) Hellwig, J.; Belser, T.; Muller, J. F. K. Tetrahedron Lett. 2001, 42, 5417. (d) Iseki, K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Tetrahedron Lett. 1998, 39, 2767. (e) Iseki, K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Tetrahedron 1999, 55, 977. (f) Nakajima, M.; Saito, M.; Shiro, M.; Hashimoto, S. J. Am. Chem. Soc. 1998, 120, 6419. (g) Malkov, A. V.; Orsini, M.; Pernazza, D.; Muir, K. W.; Langer, V.; Meghani, P.; Kocovsky, P. Org. Lett. 2002, 4, 1047. (h) Shimada, T.; Kina, A.; Ikeda, S.; Hayashi, T. Org. Lett. 2002, 4, 2799. (i) Chataigner, I.; Piarulli, U.; Gennari, C. Tetrahedron Lett. 1999, 40, 3633. (j) Angell, R. M.; Barrett, A. G. M.; Braddock, D. C.; Swallow, S.; Vickery, B. D. Chem. Commun. 1997, 919.
32. Reference on other chiral-Lewis-base-catalyzed enantioselective allylation reactions: (a) Iseki, K.; Kuroki, Y.; Takahashi, M.; Kobayashi, Y. Tetrahedron Lett. 1996, 37, 5149. (b) Iseki, K.; Kuroki, Y.; Takahashi, M.; Kishimoto, S.; Kobayashi, Y. Tetrahedron 1997, 53, 3513. (c) Hellwig, J.; Belser, T.; Muller, J. F. K. Tetrahedron Lett. 2001, 42, 5417. (d) Iseki, K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Tetrahedron Lett. 1998, 39, 2767. (e) Iseki, K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Tetrahedron 1999, 55, 977. (f) Nakajima, M.; Saito, M.; Shiro, M.; Hashimoto, S. J. Am. Chem. Soc. 1998, 120, 6419. (g) Malkov, A. V.; Orsini, M.; Pernazza, D.; Muir, K. W.; Langer, V.; Meghani, P.; Kocovsky, P. Org. Lett. 2002, 4, 1047. (h) Shimada, T.; Kina, A.; Ikeda, S.; Hayashi, T. Org. Lett. 2002, 4, 2799. (i) Chataigner, I.; Piarulli, U.; Gennari, C. Tetrahedron Lett. 1999, 40, 3633. (j) Angell, R. M.; Barrett, A. G. M.; Braddock, D. C.; Swallow, S.; Vickery, B. D. Chem. Commun. 1997, 919.
33. Reference on other chiral-Lewis-base-catalyzed enantioselective allylation reactions: (a) Iseki, K.; Kuroki, Y.; Takahashi, M.; Kobayashi, Y. Tetrahedron Lett. 1996, 37, 5149. (b) Iseki, K.; Kuroki, Y.; Takahashi, M.; Kishimoto, S.; Kobayashi, Y. Tetrahedron 1997, 53, 3513. (c) Hellwig, J.; Belser, T.; Muller, J. F. K. Tetrahedron Lett. 2001, 42, 5417. (d) Iseki, K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Tetrahedron Lett. 1998, 39, 2767. (e) Iseki, K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Tetrahedron 1999, 55, 977. (f) Nakajima, M.; Saito, M.; Shiro, M.; Hashimoto, S. J. Am. Chem. Soc. 1998, 120, 6419. (g) Malkov, A. V.; Orsini, M.; Pernazza, D.; Muir, K. W.; Langer, V.; Meghani, P.; Kocovsky, P. Org. Lett. 2002, 4, 1047. (h) Shimada, T.; Kina, A.; Ikeda, S.; Hayashi, T. Org. Lett. 2002, 4, 2799. (i) Chataigner, I.; Piarulli, U.; Gennari, C. Tetrahedron Lett. 1999, 40, 3633. (j) Angell, R. M.; Barrett, A. G. M.; Braddock, D. C.; Swallow, S.; Vickery, B. D. Chem. Commun. 1997, 919.
34. Denmark, S. E.; Ghosh, S. K. Angew. Chem., Int. Ed. 2001, 40, 4759.
35. Another study on the operativity of dimeric catalysts tethered with methylene units: Konsler, R. G.; Karl, J.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 10780.
36. For a review on the ligand bite angle effect of the phosphine ligand: van Leeuwen, P. W. N. M.; Kamer, P. C. J.; Reek, J. N. H.; Dierkes, P. Chem. Rev. 2000, 100, 2741.
37. Aslanov, L. A.; Ionov, V. M.; Attiya, V. M.; Permin, A. B.; Petrosyan, V. S. Zh. Strukt. Khim. 1977, 18, 1103.
38. Denmark, S. E.; Su, X. Tetrahedron 1999, 55, 8727.
39. (a) Ruzicka, S. J.; Favez, C. M. P.; Merbach, A. E. Inorg. Chim. Acta 1977, 23, 239.
40. (b) Ruzicka, S. J.; Merbach, A. E. Inorg. Chim. Acta 1977, 22, 191.
41. (c) Ruzicka, S. J.; Merbach, A. E. Inorg. Chim. Acta 1976, 20, 221.
42. 4 have been deposited with the Cambridge Crystallographic Data Centre; deposition no. CCDC 195246. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, U.K.; fax: (+44) 1223-336-033; or deposit@ccdc.cam.ac.uk)
43. 119Sn NMR spectrum.
44. In chiral Lewis base-catalyzed aldol reactions, kinetic isotope effect studies revealed that the rate-determining step is the addition of the nucleophile to complexed aldehyde: Pham, S. M.; Bui, T., unpublished results from these laboratories.
45. Reviews on the reactivity of hypercoordinate silicon compounds: (a) Kost, D.; Kalikhman, I. In The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y., Eds.; Wiley: Chichester, 1998; Vol. 2, Part 2, pp 1339. (b) Holmes, R. R. Chem. Rev. 1996, 96, 927. (c) Chuit, C.; Corriu, R. J. P.; Reye, C.; Young, J. C. Chem. Rev. 1993, 93, 1371. (d) Tandura, S. N.; Voronkov, M. G.; Alekseev, N. V. Top. Curr. Chem. 1986, 131, 99.
46. Reviews on the reactivity of hypercoordinate silicon compounds: (a) Kost, D.; Kalikhman, I. In The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y., Eds.; Wiley: Chichester, 1998; Vol. 2, Part 2, pp 1339. (b) Holmes, R. R. Chem. Rev. 1996, 96, 927. (c) Chuit, C.; Corriu, R. J. P.; Reye, C.; Young, J. C. Chem. Rev. 1993, 93, 1371. (d) Tandura, S. N.; Voronkov, M. G.; Alekseev, N. V. Top. Curr. Chem. 1986, 131, 99.
47. Reviews on the reactivity of hypercoordinate silicon compounds: (a) Kost, D.; Kalikhman, I. In The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y., Eds.; Wiley: Chichester, 1998; Vol. 2, Part 2, pp 1339. (b) Holmes, R. R. Chem. Rev. 1996, 96, 927. (c) Chuit, C.; Corriu, R. J. P.; Reye, C.; Young, J. C. Chem. Rev. 1993, 93, 1371. (d) Tandura, S. N.; Voronkov, M. G.; Alekseev, N. V. Top. Curr. Chem. 1986, 131, 99.
48. Reviews on the reactivity of hypercoordinate silicon compounds: (a) Kost, D.; Kalikhman, I. In The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y., Eds.; Wiley: Chichester, 1998; Vol. 2, Part 2, pp 1339. (b) Holmes, R. R. Chem. Rev. 1996, 96, 927. (c) Chuit, C.; Corriu, R. J. P.; Reye, C.; Young, J. C. Chem. Rev. 1993, 93, 1371. (d) Tandura, S. N.; Voronkov, M. G.; Alekseev, N. V. Top. Curr. Chem. 1986, 131, 99.
49. Reviews on the trans effect and ligand donor abilities: (a) Coe, B. J.; Glenwright, S. J. Coord. Chem. Rev. 2000, 203, 5. (b) Appleton, T. G.; Clark, H. C.; Manzer, L. E. Coord. Chem. Rev. 1973, 10, 335.
50. Reviews on the trans effect and ligand donor abilities: (a) Coe, B. J.; Glenwright, S. J. Coord. Chem. Rev. 2000, 203, 5. (b) Appleton, T. G.; Clark, H. C.; Manzer, L. E. Coord. Chem. Rev. 1973, 10, 335.