Electronic effects in asymmetric catalysis. Synthesis and structure of model rhodium complexes containing ferrocenyl ligands for use in the hydroboration reaction

Organometallics

Volumn 16, Issue 2, 1997, Pages 255-260

  Schnyder, Anita ^a   Togni, Antonio ^a   Wiesli, Ursula ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 5244365351     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9605995     Document Type: Article

References (43)

1. (a) Burckhardt, U.; Hintermann, L.; Schnyder, A.; Togni, A.; Organometallics, 1995, 14, 5415.
2. (b) Schnyder A., Hintermann, L.; Togni, A. Angew. Chem. 1995, 107, 996-998; Angew. Chem., Int. Ed. Engl. 1995, 34, 931-933.
3. (b) Schnyder A., Hintermann, L.; Togni, A. Angew. Chem. 1995, 107, 996-998; Angew. Chem., Int. Ed. Engl. 1995, 34, 931-933.
4. (c) Togni, A.; Burckhardt, U.; Gramlich, V.; Pregosin, P. S. P.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031.
5. (d) Burckhardt, U.; Gramlich, V.; Hofmann, P.; Nesper, R.; Pregosin, P. S.P.; Salzmann, R.; Togni, A. Organometallics 1996, 15, 3496.
6. For mechanistic considerations, see, e.g.: (a) Burgess, K.; Ohlmeyer, M. J. Adv. Chem. Ser. 1992, No. 230, 163. (b) Burgess, K.; Ohlmeyer, M. J. Chem. Rev. 1991, 91, 1191. For a recent theoretical study, see: (c) Musaev, D. G.; Mebel, A. M.; Morokuma, K. J. Am. Chem. Soc. 1994, 116, 10693.
7. For mechanistic considerations, see, e.g.: (a) Burgess, K.; Ohlmeyer, M. J. Adv. Chem. Ser. 1992, No. 230, 163. (b) Burgess, K.; Ohlmeyer, M. J. Chem. Rev. 1991, 91, 1191. For a recent theoretical study, see: (c) Musaev, D. G.; Mebel, A. M.; Morokuma, K. J. Am. Chem. Soc. 1994, 116, 10693.
8. For mechanistic considerations, see, e.g.: (a) Burgess, K.; Ohlmeyer, M. J. Adv. Chem. Ser. 1992, No. 230, 163. (b) Burgess, K.; Ohlmeyer, M. J. Chem. Rev. 1991, 91, 1191. For a recent theoretical study, see: (c) Musaev, D. G.; Mebel, A. M.; Morokuma, K. J. Am. Chem. Soc. 1994, 116, 10693.
9. (a) Van Gaal, H. L. M.; Moers, F. G.; Steggerda, J. J. J. Organomet. Chem. 1974, 65, C43.
10. (b) Kono, H.; Ito, K.; Nagai, Y. Chem. Lett. 1975, 1095.
11. (c) Busetto, C.; D'Alfonso, A.; Maspero, F.; Perego, G.; Zazetta, A. J. Chem. Soc., Dalton Trans. 1977, 1828.
12. (d) Fryzuk, M. D. Inorg. Chem. 1982, 21, 2134.
13. (e) Baker, R. T.; Ovenall, D. W.; Calabrese, J. C.; Westcott, S. A.; Williams, L. D.; Taylor, N. J.; Marder, T. B. J. Am. Chem. Soc. 1990, 112, 9399.
14. (f) Korr, J. R.; Merola, J. S. Organometallics 1990, 9, 3008.
15. (g) Westcott, S. A.; Taylor, N. J.; Marder, T. B.; Baker, R. T.; Jones, N. J.; Calabrese, J. C. J. Chem. Soc., Chem. Commun. 1991, 304.
16. (h) Burgess, K.; van der Donk, W. A.; Westcott, S. A.; Marder, T. B.; Calabrese, J. C. J. Am. Chem. Soc. 1992, 114, 9350.
17. (i) Baker, R. T.; Calabrese, J. C. J. Am. Chem. Soc. 1993, 115, 4367.
18. (j) Westcott, S. A.; Marder, T. B.; Baker, R. T.; Calabrese, J. C. Can. J. Chem. 1993, 71, 930.
19. (k) Nguyen, P.; Lesley, G.; Taylor, N. J.; Marder, T. B.; Pickett, N. L.; Clegg, W.; Elsegood, M. R. J.; Norman, N. C. Inorg. Chem. 1994, 33, 4623.
20. (l) Cleary, B. P.; Eisenberg, R. Organometallics 1995, 14, 4525.
21. For early work on Rh complexes containing P,N ligands, see, e.g.: (a) Rauchfuss, T. B.; Roundhill, D. M. J. Am. Chem. Soc. 1974, 96, 3098. (b) Cullen, W. R.; Einstein, F. W. B.; Huang, C.-H.; Willis, A. C.; Yeh, E.-S. J. Am. Chem. Soc. 1980, 102, 988.
22. For early work on Rh complexes containing P,N ligands, see, e.g.: (a) Rauchfuss, T. B.; Roundhill, D. M. J. Am. Chem. Soc. 1974, 96, 3098. (b) Cullen, W. R.; Einstein, F. W. B.; Huang, C.-H.; Willis, A. C.; Yeh, E.-S. J. Am. Chem. Soc. 1980, 102, 988.
23. 3 ligands; were correlated to the steric and electronic properties of the tris(pyrazolyl)borate ligand. See: (b) Kitajima, N.; Tolman, W. B. Prog. Inorg. Chem. 1995, 43, 419 and references therein.
24. 3 ligands; were correlated to the steric and electronic properties of the tris(pyrazolyl)borate ligand. See: (b) Kitajima, N.; Tolman, W. B. Prog. Inorg. Chem. 1995, 43, 419 and references therein.
25. Fryzuk, M. D.; Bosnich, B. J. Am. Chem Soc. 1977, 99, 6702.
26. (a) Orpen, A. G.; Brammer, L.; Allen, F. H.; Kennard, O.; Watson, D. G.; Taylor, R. J. Chem. Soc., Dalton Trans. 1989, Supplement S1-883.
27. (b) Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. J. Chem. Soc., Perkin Trans 2 1987, Supplement S1-S19.
28. See also: (c) Bürgi, H.-B., Dunitz, J. D., Eds. Structure Correlation, VCH: Weinheim, Germany, 1994; Vol. 2, Appendix A.
29. Electronic effects in asymmetric catalysis with other types of ligands have been recently reported. Rh-catalyzed hydrogenation: (a) Inoguchi, K.; Sakuraba, S.; Achiwa, K. Synlett 1992, 169 and references cited therein. (b) RajanBabu, T. V.; Ayers, T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4101. Ru-catalyzed hydrogenation with BINAP-type ligands: (c) Mashima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064. Nicatalyzed hydrocyanation of vinylarenes: (d) Casalnuovo, A. L.; RajanBabu, T. V.; Ayers, T. A.; Warren, T. H. J. Am. Chem. Soc. 1994, 116, 9869. (e) RajanBabu, T. V.; Casalnuovo, A. L. Pure Appl. Chem. 1994, 66, 1535. (f) RajanBabu, T. V.; Casalnuovo, A. L. J. Am. Chem. Soc. 1992, 114, 6265. Rh-catalyzed hydroformylation of olefins: (g) RajanBabu, T. V.; Ayers, T. A. Tetrahedron Lett. 1994, 35, 4295. Mn-catalyzed epoxidation of unfunctionalized olefins: (h) Jacobsen, E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; pp 159-202, and references cited therein. Rh-catalyzed hydrosilylation of ketones: (i) Nishiyama, H.; Yamaguchi, S.; Kondo, M.; Itoh, K. J. Org. Chem. 1992, 57, 4306. For electronically controlled stoichiometric reactions of Mo-allyl complexes, see: (j) Faller, J. W.; Chao, K.-H. J. Am. Chem. Soc. 1983, 105, 3893. (k) Faller, J. W.; Nguyen, J. T.; Ellis, W.; Mazzieri, M. R. Organometallics 1993, 12, 1434.
30. Electronic effects in asymmetric catalysis with other types of ligands have been recently reported. Rh-catalyzed hydrogenation: (a) Inoguchi, K.; Sakuraba, S.; Achiwa, K. Synlett 1992, 169 and references cited therein. (b) RajanBabu, T. V.; Ayers, T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4101. Ru-catalyzed hydrogenation with BINAP-type ligands: (c) Mashima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064. Nicatalyzed hydrocyanation of vinylarenes: (d) Casalnuovo, A. L.; RajanBabu, T. V.; Ayers, T. A.; Warren, T. H. J. Am. Chem. Soc. 1994, 116, 9869. (e) RajanBabu, T. V.; Casalnuovo, A. L. Pure Appl. Chem. 1994, 66, 1535. (f) RajanBabu, T. V.; Casalnuovo, A. L. J. Am. Chem. Soc. 1992, 114, 6265. Rh-catalyzed hydroformylation of olefins: (g) RajanBabu, T. V.; Ayers, T. A. Tetrahedron Lett. 1994, 35, 4295. Mn-catalyzed epoxidation of unfunctionalized olefins: (h) Jacobsen, E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; pp 159-202, and references cited therein. Rh-catalyzed hydrosilylation of ketones: (i) Nishiyama, H.; Yamaguchi, S.; Kondo, M.; Itoh, K. J. Org. Chem. 1992, 57, 4306. For electronically controlled stoichiometric reactions of Mo-allyl complexes, see: (j) Faller, J. W.; Chao, K.-H. J. Am. Chem. Soc. 1983, 105, 3893. (k) Faller, J. W.; Nguyen, J. T.; Ellis, W.; Mazzieri, M. R. Organometallics 1993, 12, 1434.
31. Electronic effects in asymmetric catalysis with other types of ligands have been recently reported. Rh-catalyzed hydrogenation: (a) Inoguchi, K.; Sakuraba, S.; Achiwa, K. Synlett 1992, 169 and references cited therein. (b) RajanBabu, T. V.; Ayers, T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4101. Ru-catalyzed hydrogenation with BINAP-type ligands: (c) Mashima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064. Nicatalyzed hydrocyanation of vinylarenes: (d) Casalnuovo, A. L.; RajanBabu, T. V.; Ayers, T. A.; Warren, T. H. J. Am. Chem. Soc. 1994, 116, 9869. (e) RajanBabu, T. V.; Casalnuovo, A. L. Pure Appl. Chem. 1994, 66, 1535. (f) RajanBabu, T. V.; Casalnuovo, A. L. J. Am. Chem. Soc. 1992, 114, 6265. Rh-catalyzed hydroformylation of olefins: (g) RajanBabu, T. V.; Ayers, T. A. Tetrahedron Lett. 1994, 35, 4295. Mn-catalyzed epoxidation of unfunctionalized olefins: (h) Jacobsen, E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; pp 159-202, and references cited therein. Rh-catalyzed hydrosilylation of ketones: (i) Nishiyama, H.; Yamaguchi, S.; Kondo, M.; Itoh, K. J. Org. Chem. 1992, 57, 4306. For electronically controlled stoichiometric reactions of Mo-allyl complexes, see: (j) Faller, J. W.; Chao, K.-H. J. Am. Chem. Soc. 1983, 105, 3893. (k) Faller, J. W.; Nguyen, J. T.; Ellis, W.; Mazzieri, M. R. Organometallics 1993, 12, 1434.
32. Electronic effects in asymmetric catalysis with other types of ligands have been recently reported. Rh-catalyzed hydrogenation: (a) Inoguchi, K.; Sakuraba, S.; Achiwa, K. Synlett 1992, 169 and references cited therein. (b) RajanBabu, T. V.; Ayers, T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4101. Ru-catalyzed hydrogenation with BINAP-type ligands: (c) Mashima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064. Nicatalyzed hydrocyanation of vinylarenes: (d) Casalnuovo, A. L.; RajanBabu, T. V.; Ayers, T. A.; Warren, T. H. J. Am. Chem. Soc. 1994, 116, 9869. (e) RajanBabu, T. V.; Casalnuovo, A. L. Pure Appl. Chem. 1994, 66, 1535. (f) RajanBabu, T. V.; Casalnuovo, A. L. J. Am. Chem. Soc. 1992, 114, 6265. Rh-catalyzed hydroformylation of olefins: (g) RajanBabu, T. V.; Ayers, T. A. Tetrahedron Lett. 1994, 35, 4295. Mn-catalyzed epoxidation of unfunctionalized olefins: (h) Jacobsen, E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; pp 159-202, and references cited therein. Rh-catalyzed hydrosilylation of ketones: (i) Nishiyama, H.; Yamaguchi, S.; Kondo, M.; Itoh, K. J. Org. Chem. 1992, 57, 4306. For electronically controlled stoichiometric reactions of Mo-allyl complexes, see: (j) Faller, J. W.; Chao, K.-H. J. Am. Chem. Soc. 1983, 105, 3893. (k) Faller, J. W.; Nguyen, J. T.; Ellis, W.; Mazzieri, M. R. Organometallics 1993, 12, 1434.
33. Electronic effects in asymmetric catalysis with other types of ligands have been recently reported. Rh-catalyzed hydrogenation: (a) Inoguchi, K.; Sakuraba, S.; Achiwa, K. Synlett 1992, 169 and references cited therein. (b) RajanBabu, T. V.; Ayers, T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4101. Ru-catalyzed hydrogenation with BINAP-type ligands: (c) Mashima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064. Nicatalyzed hydrocyanation of vinylarenes: (d) Casalnuovo, A. L.; RajanBabu, T. V.; Ayers, T. A.; Warren, T. H. J. Am. Chem. Soc. 1994, 116, 9869. (e) RajanBabu, T. V.; Casalnuovo, A. L. Pure Appl. Chem. 1994, 66, 1535. (f) RajanBabu, T. V.; Casalnuovo, A. L. J. Am. Chem. Soc. 1992, 114, 6265. Rh-catalyzed hydroformylation of olefins: (g) RajanBabu, T. V.; Ayers, T. A. Tetrahedron Lett. 1994, 35, 4295. Mn-catalyzed epoxidation of unfunctionalized olefins: (h) Jacobsen, E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; pp 159-202, and references cited therein. Rh-catalyzed hydrosilylation of ketones: (i) Nishiyama, H.; Yamaguchi, S.; Kondo, M.; Itoh, K. J. Org. Chem. 1992, 57, 4306. For electronically controlled stoichiometric reactions of Mo-allyl complexes, see: (j) Faller, J. W.; Chao, K.-H. J. Am. Chem. Soc. 1983, 105, 3893. (k) Faller, J. W.; Nguyen, J. T.; Ellis, W.; Mazzieri, M. R. Organometallics 1993, 12, 1434.
34. Electronic effects in asymmetric catalysis with other types of ligands have been recently reported. Rh-catalyzed hydrogenation: (a) Inoguchi, K.; Sakuraba, S.; Achiwa, K. Synlett 1992, 169 and references cited therein. (b) RajanBabu, T. V.; Ayers, T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4101. Ru-catalyzed hydrogenation with BINAP-type ligands: (c) Mashima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064. Nicatalyzed hydrocyanation of vinylarenes: (d) Casalnuovo, A. L.; RajanBabu, T. V.; Ayers, T. A.; Warren, T. H. J. Am. Chem. Soc. 1994, 116, 9869. (e) RajanBabu, T. V.; Casalnuovo, A. L. Pure Appl. Chem. 1994, 66, 1535. (f) RajanBabu, T. V.; Casalnuovo, A. L. J. Am. Chem. Soc. 1992, 114, 6265. Rh-catalyzed hydroformylation of olefins: (g) RajanBabu, T. V.; Ayers, T. A. Tetrahedron Lett. 1994, 35, 4295. Mn-catalyzed epoxidation of unfunctionalized olefins: (h) Jacobsen, E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; pp 159-202, and references cited therein. Rh-catalyzed hydrosilylation of ketones: (i) Nishiyama, H.; Yamaguchi, S.; Kondo, M.; Itoh, K. J. Org. Chem. 1992, 57, 4306. For electronically controlled stoichiometric reactions of Mo-allyl complexes, see: (j) Faller, J. W.; Chao, K.-H. J. Am. Chem. Soc. 1983, 105, 3893. (k) Faller, J. W.; Nguyen, J. T.; Ellis, W.; Mazzieri, M. R. Organometallics 1993, 12, 1434.
35. Electronic effects in asymmetric catalysis with other types of ligands have been recently reported. Rh-catalyzed hydrogenation: (a) Inoguchi, K.; Sakuraba, S.; Achiwa, K. Synlett 1992, 169 and references cited therein. (b) RajanBabu, T. V.; Ayers, T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4101. Ru-catalyzed hydrogenation with BINAP-type ligands: (c) Mashima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064. Nicatalyzed hydrocyanation of vinylarenes: (d) Casalnuovo, A. L.; RajanBabu, T. V.; Ayers, T. A.; Warren, T. H. J. Am. Chem. Soc. 1994, 116, 9869. (e) RajanBabu, T. V.; Casalnuovo, A. L. Pure Appl. Chem. 1994, 66, 1535. (f) RajanBabu, T. V.; Casalnuovo, A. L. J. Am. Chem. Soc. 1992, 114, 6265. Rh-catalyzed hydroformylation of olefins: (g) RajanBabu, T. V.; Ayers, T. A. Tetrahedron Lett. 1994, 35, 4295. Mn-catalyzed epoxidation of unfunctionalized olefins: (h) Jacobsen, E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; pp 159-202, and references cited therein. Rh-catalyzed hydrosilylation of ketones: (i) Nishiyama, H.; Yamaguchi, S.; Kondo, M.; Itoh, K. J. Org. Chem. 1992, 57, 4306. For electronically controlled stoichiometric reactions of Mo-allyl complexes, see: (j) Faller, J. W.; Chao, K.-H. J. Am. Chem. Soc. 1983, 105, 3893. (k) Faller, J. W.; Nguyen, J. T.; Ellis, W.; Mazzieri, M. R. Organometallics 1993, 12, 1434.
36. Electronic effects in asymmetric catalysis with other types of ligands have been recently reported. Rh-catalyzed hydrogenation: (a) Inoguchi, K.; Sakuraba, S.; Achiwa, K. Synlett 1992, 169 and references cited therein. (b) RajanBabu, T. V.; Ayers, T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4101. Ru-catalyzed hydrogenation with BINAP-type ligands: (c) Mashima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064. Nicatalyzed hydrocyanation of vinylarenes: (d) Casalnuovo, A. L.; RajanBabu, T. V.; Ayers, T. A.; Warren, T. H. J. Am. Chem. Soc. 1994, 116, 9869. (e) RajanBabu, T. V.; Casalnuovo, A. L. Pure Appl. Chem. 1994, 66, 1535. (f) RajanBabu, T. V.; Casalnuovo, A. L. J. Am. Chem. Soc. 1992, 114, 6265. Rh-catalyzed hydroformylation of olefins: (g) RajanBabu, T. V.; Ayers, T. A. Tetrahedron Lett. 1994, 35, 4295. Mn-catalyzed epoxidation of unfunctionalized olefins: (h) Jacobsen, E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; pp 159-202, and references cited therein. Rh-catalyzed hydrosilylation of ketones: (i) Nishiyama, H.; Yamaguchi, S.; Kondo, M.; Itoh, K. J. Org. Chem. 1992, 57, 4306. For electronically controlled stoichiometric reactions of Mo-allyl complexes, see: (j) Faller, J. W.; Chao, K.-H. J. Am. Chem. Soc. 1983, 105, 3893. (k) Faller, J. W.; Nguyen, J. T.; Ellis, W.; Mazzieri, M. R. Organometallics 1993, 12, 1434.
37. Electronic effects in asymmetric catalysis with other types of ligands have been recently reported. Rh-catalyzed hydrogenation: (a) Inoguchi, K.; Sakuraba, S.; Achiwa, K. Synlett 1992, 169 and references cited therein. (b) RajanBabu, T. V.; Ayers, T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4101. Ru-catalyzed hydrogenation with BINAP-type ligands: (c) Mashima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064. Nicatalyzed hydrocyanation of vinylarenes: (d) Casalnuovo, A. L.; RajanBabu, T. V.; Ayers, T. A.; Warren, T. H. J. Am. Chem. Soc. 1994, 116, 9869. (e) RajanBabu, T. V.; Casalnuovo, A. L. Pure Appl. Chem. 1994, 66, 1535. (f) RajanBabu, T. V.; Casalnuovo, A. L. J. Am. Chem. Soc. 1992, 114, 6265. Rh-catalyzed hydroformylation of olefins: (g) RajanBabu, T. V.; Ayers, T. A. Tetrahedron Lett. 1994, 35, 4295. Mn-catalyzed epoxidation of unfunctionalized olefins: (h) Jacobsen, E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; pp 159-202, and references cited therein. Rh-catalyzed hydrosilylation of ketones: (i) Nishiyama, H.; Yamaguchi, S.; Kondo, M.; Itoh, K. J. Org. Chem. 1992, 57, 4306. For electronically controlled stoichiometric reactions of Mo-allyl complexes, see: (j) Faller, J. W.; Chao, K.-H. J. Am. Chem. Soc. 1983, 105, 3893. (k) Faller, J. W.; Nguyen, J. T.; Ellis, W.; Mazzieri, M. R. Organometallics 1993, 12, 1434.
38. Electronic effects in asymmetric catalysis with other types of ligands have been recently reported. Rh-catalyzed hydrogenation: (a) Inoguchi, K.; Sakuraba, S.; Achiwa, K. Synlett 1992, 169 and references cited therein. (b) RajanBabu, T. V.; Ayers, T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4101. Ru-catalyzed hydrogenation with BINAP-type ligands: (c) Mashima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064. Nicatalyzed hydrocyanation of vinylarenes: (d) Casalnuovo, A. L.; RajanBabu, T. V.; Ayers, T. A.; Warren, T. H. J. Am. Chem. Soc. 1994, 116, 9869. (e) RajanBabu, T. V.; Casalnuovo, A. L. Pure Appl. Chem. 1994, 66, 1535. (f) RajanBabu, T. V.; Casalnuovo, A. L. J. Am. Chem. Soc. 1992, 114, 6265. Rh-catalyzed hydroformylation of olefins: (g) RajanBabu, T. V.; Ayers, T. A. Tetrahedron Lett. 1994, 35, 4295. Mn-catalyzed epoxidation of unfunctionalized olefins: (h) Jacobsen, E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; pp 159-202, and references cited therein. Rh-catalyzed hydrosilylation of ketones: (i) Nishiyama, H.; Yamaguchi, S.; Kondo, M.; Itoh, K. J. Org. Chem. 1992, 57, 4306. For electronically controlled stoichiometric reactions of Mo-allyl complexes, see: (j) Faller, J. W.; Chao, K.-H. J. Am. Chem. Soc. 1983, 105, 3893. (k) Faller, J. W.; Nguyen, J. T.; Ellis, W.; Mazzieri, M. R. Organometallics 1993, 12, 1434.
39. Electronic effects in asymmetric catalysis with other types of ligands have been recently reported. Rh-catalyzed hydrogenation: (a) Inoguchi, K.; Sakuraba, S.; Achiwa, K. Synlett 1992, 169 and references cited therein. (b) RajanBabu, T. V.; Ayers, T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4101. Ru-catalyzed hydrogenation with BINAP-type ligands: (c) Mashima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064. Nicatalyzed hydrocyanation of vinylarenes: (d) Casalnuovo, A. L.; RajanBabu, T. V.; Ayers, T. A.; Warren, T. H. J. Am. Chem. Soc. 1994, 116, 9869. (e) RajanBabu, T. V.; Casalnuovo, A. L. Pure Appl. Chem. 1994, 66, 1535. (f) RajanBabu, T. V.; Casalnuovo, A. L. J. Am. Chem. Soc. 1992, 114, 6265. Rh-catalyzed hydroformylation of olefins: (g) RajanBabu, T. V.; Ayers, T. A. Tetrahedron Lett. 1994, 35, 4295. Mn-catalyzed epoxidation of unfunctionalized olefins: (h) Jacobsen, E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; pp 159-202, and references cited therein. Rh-catalyzed hydrosilylation of ketones: (i) Nishiyama, H.; Yamaguchi, S.; Kondo, M.; Itoh, K. J. Org. Chem. 1992, 57, 4306. For electronically controlled stoichiometric reactions of Mo-allyl complexes, see: (j) Faller, J. W.; Chao, K.-H. J. Am. Chem. Soc. 1983, 105, 3893. (k) Faller, J. W.; Nguyen, J. T.; Ellis, W.; Mazzieri, M. R. Organometallics 1993, 12, 1434.
40. For a quantitative approach to ligand effects, see: (a) Bartholomew, J.; Fernandez, A.; Lorsbach, B. A.; Giering, W. P. Organometallics 1996, 15, 295 and references cited therein. For recent general references concerning steric effects, see: (b) Brown, T. L.; Lee, K. J. Coord. Chem. Rev. 1993, 128, 89. (c) Data, D.; Majumdar, D. J. Phys. Org. Chem. 1991, 4, 611. (d) Seligson, A. L.; Trogler, W. C. J. Am. Chem. Soc. 1991, 113, 2520.
41. For a quantitative approach to ligand effects, see: (a) Bartholomew, J.; Fernandez, A.; Lorsbach, B. A.; Giering, W. P. Organometallics 1996, 15, 295 and references cited therein. For recent general references concerning steric effects, see: (b) Brown, T. L.; Lee, K. J. Coord. Chem. Rev. 1993, 128, 89. (c) Data, D.; Majumdar, D. J. Phys. Org. Chem. 1991, 4, 611. (d) Seligson, A. L.; Trogler, W. C. J. Am. Chem. Soc. 1991, 113, 2520.
42. For a quantitative approach to ligand effects, see: (a) Bartholomew, J.; Fernandez, A.; Lorsbach, B. A.; Giering, W. P. Organometallics 1996, 15, 295 and references cited therein. For recent general references concerning steric effects, see: (b) Brown, T. L.; Lee, K. J. Coord. Chem. Rev. 1993, 128, 89. (c) Data, D.; Majumdar, D. J. Phys. Org. Chem. 1991, 4, 611. (d) Seligson, A. L.; Trogler, W. C. J. Am. Chem. Soc. 1991, 113, 2520.
43. For a quantitative approach to ligand effects, see: (a) Bartholomew, J.; Fernandez, A.; Lorsbach, B. A.; Giering, W. P. Organometallics 1996, 15, 295 and references cited therein. For recent general references concerning steric effects, see: (b) Brown, T. L.; Lee, K. J. Coord. Chem. Rev. 1993, 128, 89. (c) Data, D.; Majumdar, D. J. Phys. Org. Chem. 1991, 4, 611. (d) Seligson, A. L.; Trogler, W. C. J. Am. Chem. Soc. 1991, 113, 2520.