Mechanism of palladium complex-catalyzed enantioselective mannich-type reaction: Characterization of a novel binuclear palladium enolate complex

Journal of the American Chemical Society

Volumn 121, Issue 23, 1999, Pages 5450-5458

  Fujii, Akio ^a   Hagiwara, Emiko ^a   Sodeoka, Mikiko ^a  

^a SAGAMI CHEMICAL RESEARCH CENTER   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

MANNICH BASE; PALLADIUM COMPLEX;

ARTICLE; CATALYSIS; CHIRALITY; COMPLEX FORMATION; CONFORMATIONAL TRANSITION; DRUG SYNTHESIS; HALOGENATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0033575073     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9902827     Document Type: Article

References (75)

1. For reviews, see: (a) Kleinman, E. F. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: New York, 1991; Vol. 2, pp 893-951. (b) Hart, D. J.; Ha, D.-C. Chem. Rev. 1989, 89, 1447-1465. (c) Arend, M.; Westermann, B.; Risch, N. Angew. Chem., Int. Ed. 1998, 37, 1044-1070 and references therein.
2. For reviews, see: (a) Kleinman, E. F. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: New York, 1991; Vol. 2, pp 893-951. (b) Hart, D. J.; Ha, D.-C. Chem. Rev. 1989, 89, 1447-1465. (c) Arend, M.; Westermann, B.; Risch, N. Angew. Chem., Int. Ed. 1998, 37, 1044-1070 and references therein.
3. For reviews, see: (a) Kleinman, E. F. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: New York, 1991; Vol. 2, pp 893-951. (b) Hart, D. J.; Ha, D.-C. Chem. Rev. 1989, 89, 1447-1465. (c) Arend, M.; Westermann, B.; Risch, N. Angew. Chem., Int. Ed. 1998, 37, 1044-1070 and references therein.
4. For reactions using a stoichiometric amount of chiral source, see: (a) Corey, E. J.; Decicco, C. P.; Newbold, R. C. Tetrahedron Lett. 1991, 32, 5287-5290. (b) Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10520-10524. (c) Kambara, T.; Hussein, A.; Fujieda, H.; Iida, A.; Tomioka, K. Teterahedron Lett. 1998, 39, 9055-9058. For reactions using a catalytic amount of chiral source, see: (d) Fujieda, H.; Kanal, M.; Kambara, T.; Iida, A.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 2060-2061. (e) Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153-7154. (f) Kobayashi, S.; Ishitani, H.; Ueno, M. J. Am. Chem. Soc. 1998, 120, 431-432. (g) Yamasaki, S.; Iida, T.; Shibasaki, M. Tetrahedron Lett. 1999, 40, 307-310.
5. For reactions using a stoichiometric amount of chiral source, see: (a) Corey, E. J.; Decicco, C. P.; Newbold, R. C. Tetrahedron Lett. 1991, 32, 5287-5290. (b) Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10520-10524. (c) Kambara, T.; Hussein, A.; Fujieda, H.; Iida, A.; Tomioka, K. Teterahedron Lett. 1998, 39, 9055-9058. For reactions using a catalytic amount of chiral source, see: (d) Fujieda, H.; Kanal, M.; Kambara, T.; Iida, A.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 2060-2061. (e) Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153-7154. (f) Kobayashi, S.; Ishitani, H.; Ueno, M. J. Am. Chem. Soc. 1998, 120, 431-432. (g) Yamasaki, S.; Iida, T.; Shibasaki, M. Tetrahedron Lett. 1999, 40, 307-310.
6. For reactions using a stoichiometric amount of chiral source, see: (a) Corey, E. J.; Decicco, C. P.; Newbold, R. C. Tetrahedron Lett. 1991, 32, 5287-5290. (b) Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10520-10524. (c) Kambara, T.; Hussein, A.; Fujieda, H.; Iida, A.; Tomioka, K. Teterahedron Lett. 1998, 39, 9055-9058. For reactions using a catalytic amount of chiral source, see: (d) Fujieda, H.; Kanal, M.; Kambara, T.; Iida, A.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 2060-2061. (e) Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153-7154. (f) Kobayashi, S.; Ishitani, H.; Ueno, M. J. Am. Chem. Soc. 1998, 120, 431-432. (g) Yamasaki, S.; Iida, T.; Shibasaki, M. Tetrahedron Lett. 1999, 40, 307-310.
7. For reactions using a stoichiometric amount of chiral source, see: (a) Corey, E. J.; Decicco, C. P.; Newbold, R. C. Tetrahedron Lett. 1991, 32, 5287-5290. (b) Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10520-10524. (c) Kambara, T.; Hussein, A.; Fujieda, H.; Iida, A.; Tomioka, K. Teterahedron Lett. 1998, 39, 9055-9058. For reactions using a catalytic amount of chiral source, see: (d) Fujieda, H.; Kanal, M.; Kambara, T.; Iida, A.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 2060-2061. (e) Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153-7154. (f) Kobayashi, S.; Ishitani, H.; Ueno, M. J. Am. Chem. Soc. 1998, 120, 431-432. (g) Yamasaki, S.; Iida, T.; Shibasaki, M. Tetrahedron Lett. 1999, 40, 307-310.
8. For reactions using a stoichiometric amount of chiral source, see: (a) Corey, E. J.; Decicco, C. P.; Newbold, R. C. Tetrahedron Lett. 1991, 32, 5287-5290. (b) Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10520-10524. (c) Kambara, T.; Hussein, A.; Fujieda, H.; Iida, A.; Tomioka, K. Teterahedron Lett. 1998, 39, 9055-9058. For reactions using a catalytic amount of chiral source, see: (d) Fujieda, H.; Kanal, M.; Kambara, T.; Iida, A.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 2060-2061. (e) Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153-7154. (f) Kobayashi, S.; Ishitani, H.; Ueno, M. J. Am. Chem. Soc. 1998, 120, 431-432. (g) Yamasaki, S.; Iida, T.; Shibasaki, M. Tetrahedron Lett. 1999, 40, 307-310.
9. For reactions using a stoichiometric amount of chiral source, see: (a) Corey, E. J.; Decicco, C. P.; Newbold, R. C. Tetrahedron Lett. 1991, 32, 5287-5290. (b) Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10520-10524. (c) Kambara, T.; Hussein, A.; Fujieda, H.; Iida, A.; Tomioka, K. Teterahedron Lett. 1998, 39, 9055-9058. For reactions using a catalytic amount of chiral source, see: (d) Fujieda, H.; Kanal, M.; Kambara, T.; Iida, A.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 2060-2061. (e) Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153-7154. (f) Kobayashi, S.; Ishitani, H.; Ueno, M. J. Am. Chem. Soc. 1998, 120, 431-432. (g) Yamasaki, S.; Iida, T.; Shibasaki, M. Tetrahedron Lett. 1999, 40, 307-310.
10. For reactions using a stoichiometric amount of chiral source, see: (a) Corey, E. J.; Decicco, C. P.; Newbold, R. C. Tetrahedron Lett. 1991, 32, 5287-5290. (b) Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10520-10524. (c) Kambara, T.; Hussein, A.; Fujieda, H.; Iida, A.; Tomioka, K. Teterahedron Lett. 1998, 39, 9055-9058. For reactions using a catalytic amount of chiral source, see: (d) Fujieda, H.; Kanal, M.; Kambara, T.; Iida, A.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 2060-2061. (e) Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153-7154. (f) Kobayashi, S.; Ishitani, H.; Ueno, M. J. Am. Chem. Soc. 1998, 120, 431-432. (g) Yamasaki, S.; Iida, T.; Shibasaki, M. Tetrahedron Lett. 1999, 40, 307-310.
11. Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474-2475.
12. (a) Giordani, A.; Corti, L.; Cini, M.; Brometti, R.; Marconi, M.; Veneroni, O.; Speciale, C.; Varasi, M. Recent Advances in Tryptophan Research; Plenum Press: New York, 1996; pp 531-534.
13. (b) Giordani, A.; Pevarello, P.; Cini, M.; Bormetti, R.; Greco, F.; Toma, S.; Speciale, C.; Varaqsi, M. Bioorg. Med. Chem. Lett. 1998, 8, 2907-2912 and references therein.
14. A limited number of examples of N-arylation of optically active α-amino acids and intramolecular arylation of α -amino acid ester have been reported. See: (a) Ma, D.; Yao, H. Tetrahedron: Asymmetry 1996, 7, 3075-3078. (b) Wagaw, S.; Rennels, R. A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 8451-8458. (c) Ma, D.; Zhang, Y.; Wu, S.; Tao, F. J. Am. Chem. Soc. 1998, 120, 12459-12467. For a review on the N-arylation, see: (d) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2047- 2067 and references therein.
15. A limited number of examples of N-arylation of optically active α-amino acids and intramolecular arylation of α -amino acid ester have been reported. See: (a) Ma, D.; Yao, H. Tetrahedron: Asymmetry 1996, 7, 3075-3078. (b) Wagaw, S.; Rennels, R. A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 8451-8458. (c) Ma, D.; Zhang, Y.; Wu, S.; Tao, F. J. Am. Chem. Soc. 1998, 120, 12459-12467. For a review on the N-arylation, see: (d) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2047- 2067 and references therein.
16. A limited number of examples of N-arylation of optically active α-amino acids and intramolecular arylation of α -amino acid ester have been reported. See: (a) Ma, D.; Yao, H. Tetrahedron: Asymmetry 1996, 7, 3075-3078. (b) Wagaw, S.; Rennels, R. A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 8451-8458. (c) Ma, D.; Zhang, Y.; Wu, S.; Tao, F. J. Am. Chem. Soc. 1998, 120, 12459-12467. For a review on the N-arylation, see: (d) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2047- 2067 and references therein.
17. A limited number of examples of N-arylation of optically active α-amino acids and intramolecular arylation of α -amino acid ester have been reported. See: (a) Ma, D.; Yao, H. Tetrahedron: Asymmetry 1996, 7, 3075-3078. (b) Wagaw, S.; Rennels, R. A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 8451-8458. (c) Ma, D.; Zhang, Y.; Wu, S.; Tao, F. J. Am. Chem. Soc. 1998, 120, 12459-12467. For a review on the N-arylation, see: (d) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2047-2067 and references therein.
18. (a) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548-4549.
19. (b) Ferraris, D.; Young, B.; Cox, C.; Drury, W. J. III; Dudding, T.; Lectka, T. J. Org. Chem. 1998, 63, 6090-6091.
20. (a) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648-2649.
21. (b) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463-466.
22. (c) Sodeoka, M.; Shibasaki, M. Pure Appl. Chem. 1998, 70, 411-414.
23. (a) Pisano, C.; Consiglio, G.; Sironi, A.; Moret, M. J. J. Chem. Soc., Chem. Commun. 1991, 421-423.
24. (b) Longato, B.; Pilloni, G.; Valle, G. Corain, B. Inorg. Chem. 1988, 27, 956-958.
25. (c) Bushnell, G. W.; Dixon, K. R.; Hunter, R. G.; McFarland, J. J. Can. J. Chem. 1972, 50, 3694-3699.
26. Prolonged reaction in acetone with a large amount of 4-Å molecular sieves caused byproduction of acetone dimer.
27. 7 were 2.07 and 2.45 ppm, suggesting dissociation of the binuclear μ-chloro complex to the corresponding mononuclear complex similar to 10 in the coordinating solvent.
28. For a review on ESI-MS of metal complexes, see: (a) Colton, R.; D'Agostino, A.; Traeger, J. C. Mass Spectrom. Rev. 1995, 36, 1718-1719. For examples of the use of ESI-MS to observe organometallic reaction intermediates, see: (b) Aliprantis, A. O.; Canary, J. W. J. Am. Chem. Soc 1994, 116, 6985-6986. (c) Feichtinger, D.; Plattner, D. A. Angew. Chem., Int. Ed. Engl. 1997, 36, 1718-1719. (d) Feichtinger, D.; Plattner, D. A.; Chen, P. J. Am. Chem. Soc. 1998, 120, 7125-7126 and references therein.
29. For a review on ESI-MS of metal complexes, see: (a) Colton, R.; D'Agostino, A.; Traeger, J. C. Mass Spectrom. Rev. 1995, 36, 1718-1719. For examples of the use of ESI-MS to observe organometallic reaction intermediates, see: (b) Aliprantis, A. O.; Canary, J. W. J. Am. Chem. Soc 1994, 116, 6985-6986. (c) Feichtinger, D.; Plattner, D. A. Angew. Chem., Int. Ed. Engl. 1997, 36, 1718-1719. (d) Feichtinger, D.; Plattner, D. A.; Chen, P. J. Am. Chem. Soc. 1998, 120, 7125-7126 and references therein.
30. For a review on ESI-MS of metal complexes, see: (a) Colton, R.; D'Agostino, A.; Traeger, J. C. Mass Spectrom. Rev. 1995, 36, 1718-1719. For examples of the use of ESI-MS to observe organometallic reaction intermediates, see: (b) Aliprantis, A. O.; Canary, J. W. J. Am. Chem. Soc 1994, 116, 6985-6986. (c) Feichtinger, D.; Plattner, D. A. Angew. Chem., Int. Ed. Engl. 1997, 36, 1718-1719. (d) Feichtinger, D.; Plattner, D. A.; Chen, P. J. Am. Chem. Soc. 1998, 120, 7125-7126 and references therein.
31. For a review on ESI-MS of metal complexes, see: (a) Colton, R.; D'Agostino, A.; Traeger, J. C. Mass Spectrom. Rev. 1995, 36, 1718-1719. For examples of the use of ESI-MS to observe organometallic reaction intermediates, see: (b) Aliprantis, A. O.; Canary, J. W. J. Am. Chem. Soc 1994, 116, 6985-6986. (c) Feichtinger, D.; Plattner, D. A. Angew. Chem., Int. Ed. Engl. 1997, 36, 1718-1719. (d) Feichtinger, D.; Plattner, D. A.; Chen, P. J. Am. Chem. Soc. 1998, 120, 7125-7126 and references therein.
32. Fujii, A.; Sodeoka, M., unpublished results. Reaction of 1a with benzaldehyde catalyzed by 4d (1 mol %) in wet DMF at 23 °C for 7 h gave the aldol product in 71% yield and 72% ee.
33. For a review, see: (a) Mekelburger, H. B.; Wilcox, C. S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: New York, 1991; Vol. 2, pp 99-131 and references therein. For recent selected examples of middle and late transition metal enolate complexes, see the following references. W and Mo: (b) Burkhardt, E. R.; Doney, J. J.; Slough, G. A.; Stack, J. M.; Heathcock, C. H.; Bergman, R. G. Pure Appl. Chem. 1988, 60, 1-6. (c) Faller, J. W.; Ma, Y. Organometallics 1993, 12, 1927-1930. Re: (d) Stack, J. G.; Simpson, R. D.; Hollander, F. J.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1990, 112, 2716-2729. Ru: (e) Rasley, B. T.; Rapta, M.; Kulawiec, R. J. Organometallics 1996, 15, 2852-2854. (f) Hartwig, J. F.; Bergman, R. G.; Andersen, R. A. Organometallics 1991, 10, 3326-3344. Rh and Ir: (g) Milstein, D. J. Am. Chem. Soc. 1982, 104, 5227-5228. (h) Aoyama, Y.; Yoshida, T.; Ogoshi, H. Tetrahedron Lett. 1985, 26, 6107- 6108. (i) Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1989, 111, 938-949. (j) Milstein, D.; Calabrese, J. C. J. Am. Chem. Soc. 1982, 104, 3773-3774. Pt: (k) Cairns, M. A.; Dixon, K. R.; Smith, M. A. R. J. Organomet. Chem. 1977, 135, C33-C34. (l) Arnold, D. P.; Bennett, M. A. J. Organomet. Chem. 1980, 199, 119-135. (m) Almeida, J. F.; Pidcock, A. J. Organomet. Chem. 1981, 209, 415-423. (n) Fujimura, O. J. Am. Chem. Soc. 1998, 120, 10032-10039. Cu: (o) Krüger. J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837-838 and references therein.
34. For a review, see: (a) Mekelburger, H. B.; Wilcox, C. S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: New York, 1991; Vol. 2, pp 99-131 and references therein. For recent selected examples of middle and late transition metal enolate complexes, see the following references. W and Mo: (b) Burkhardt, E. R.; Doney, J. J.; Slough, G. A.; Stack, J. M.; Heathcock, C. H.; Bergman, R. G. Pure Appl. Chem. 1988, 60, 1-6. (c) Faller, J. W.; Ma, Y. Organometallics 1993, 12, 1927-1930. Re: (d) Stack, J. G.; Simpson, R. D.; Hollander, F. J.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1990, 112, 2716-2729. Ru: (e) Rasley, B. T.; Rapta, M.; Kulawiec, R. J. Organometallics 1996, 15, 2852-2854. (f) Hartwig, J. F.; Bergman, R. G.; Andersen, R. A. Organometallics 1991, 10, 3326-3344. Rh and Ir: (g) Milstein, D. J. Am. Chem. Soc. 1982, 104, 5227-5228. (h) Aoyama, Y.; Yoshida, T.; Ogoshi, H. Tetrahedron Lett. 1985, 26, 6107- 6108. (i) Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1989, 111, 938-949. (j) Milstein, D.; Calabrese, J. C. J. Am. Chem. Soc. 1982, 104, 3773-3774. Pt: (k) Cairns, M. A.; Dixon, K. R.; Smith, M. A. R. J. Organomet. Chem. 1977, 135, C33-C34. (l) Arnold, D. P.; Bennett, M. A. J. Organomet. Chem. 1980, 199, 119-135. (m) Almeida, J. F.; Pidcock, A. J. Organomet. Chem. 1981, 209, 415-423. (n) Fujimura, O. J. Am. Chem. Soc. 1998, 120, 10032-10039. Cu: (o) Krüger. J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837-838 and references therein.
35. For a review, see: (a) Mekelburger, H. B.; Wilcox, C. S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: New York, 1991; Vol. 2, pp 99-131 and references therein. For recent selected examples of middle and late transition metal enolate complexes, see the following references. W and Mo: (b) Burkhardt, E. R.; Doney, J. J.; Slough, G. A.; Stack, J. M.; Heathcock, C. H.; Bergman, R. G. Pure Appl. Chem. 1988, 60, 1-6. (c) Faller, J. W.; Ma, Y. Organometallics 1993, 12, 1927-1930. Re: (d) Stack, J. G.; Simpson, R. D.; Hollander, F. J.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1990, 112, 2716-2729. Ru: (e) Rasley, B. T.; Rapta, M.; Kulawiec, R. J. Organometallics 1996, 15, 2852-2854. (f) Hartwig, J. F.; Bergman, R. G.; Andersen, R. A. Organometallics 1991, 10, 3326-3344. Rh and Ir: (g) Milstein, D. J. Am. Chem. Soc. 1982, 104, 5227-5228. (h) Aoyama, Y.; Yoshida, T.; Ogoshi, H. Tetrahedron Lett. 1985, 26, 6107- 6108. (i) Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1989, 111, 938-949. (j) Milstein, D.; Calabrese, J. C. J. Am. Chem. Soc. 1982, 104, 3773-3774. Pt: (k) Cairns, M. A.; Dixon, K. R.; Smith, M. A. R. J. Organomet. Chem. 1977, 135, C33-C34. (l) Arnold, D. P.; Bennett, M. A. J. Organomet. Chem. 1980, 199, 119-135. (m) Almeida, J. F.; Pidcock, A. J. Organomet. Chem. 1981, 209, 415-423. (n) Fujimura, O. J. Am. Chem. Soc. 1998, 120, 10032-10039. Cu: (o) Krüger. J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837-838 and references therein.
36. For a review, see: (a) Mekelburger, H. B.; Wilcox, C. S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: New York, 1991; Vol. 2, pp 99-131 and references therein. For recent selected examples of middle and late transition metal enolate complexes, see the following references. W and Mo: (b) Burkhardt, E. R.; Doney, J. J.; Slough, G. A.; Stack, J. M.; Heathcock, C. H.; Bergman, R. G. Pure Appl. Chem. 1988, 60, 1-6. (c) Faller, J. W.; Ma, Y. Organometallics 1993, 12, 1927-1930. Re: (d) Stack, J. G.; Simpson, R. D.; Hollander, F. J.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1990, 112, 2716-2729. Ru: (e) Rasley, B. T.; Rapta, M.; Kulawiec, R. J. Organometallics 1996, 15, 2852-2854. (f) Hartwig, J. F.; Bergman, R. G.; Andersen, R. A. Organometallics 1991, 10, 3326-3344. Rh and Ir: (g) Milstein, D. J. Am. Chem. Soc. 1982, 104, 5227-5228. (h) Aoyama, Y.; Yoshida, T.; Ogoshi, H. Tetrahedron Lett. 1985, 26, 6107- 6108. (i) Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1989, 111, 938-949. (j) Milstein, D.; Calabrese, J. C. J. Am. Chem. Soc. 1982, 104, 3773-3774. Pt: (k) Cairns, M. A.; Dixon, K. R.; Smith, M. A. R. J. Organomet. Chem. 1977, 135, C33-C34. (l) Arnold, D. P.; Bennett, M. A. J. Organomet. Chem. 1980, 199, 119-135. (m) Almeida, J. F.; Pidcock, A. J. Organomet. Chem. 1981, 209, 415-423. (n) Fujimura, O. J. Am. Chem. Soc. 1998, 120, 10032-10039. Cu: (o) Krüger. J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837-838 and references therein.
37. For a review, see: (a) Mekelburger, H. B.; Wilcox, C. S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: New York, 1991; Vol. 2, pp 99-131 and references therein. For recent selected examples of middle and late transition metal enolate complexes, see the following references. W and Mo: (b) Burkhardt, E. R.; Doney, J. J.; Slough, G. A.; Stack, J. M.; Heathcock, C. H.; Bergman, R. G. Pure Appl. Chem. 1988, 60, 1-6. (c) Faller, J. W.; Ma, Y. Organometallics 1993, 12, 1927-1930. Re: (d) Stack, J. G.; Simpson, R. D.; Hollander, F. J.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1990, 112, 2716-2729. Ru: (e) Rasley, B. T.; Rapta, M.; Kulawiec, R. J. Organometallics 1996, 15, 2852-2854. (f) Hartwig, J. F.; Bergman, R. G.; Andersen, R. A. Organometallics 1991, 10, 3326-3344. Rh and Ir: (g) Milstein, D. J. Am. Chem. Soc. 1982, 104, 5227-5228. (h) Aoyama, Y.; Yoshida, T.; Ogoshi, H. Tetrahedron Lett. 1985, 26, 6107- 6108. (i) Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1989, 111, 938-949. (j) Milstein, D.; Calabrese, J. C. J. Am. Chem. Soc. 1982, 104, 3773-3774. Pt: (k) Cairns, M. A.; Dixon, K. R.; Smith, M. A. R. J. Organomet. Chem. 1977, 135, C33-C34. (l) Arnold, D. P.; Bennett, M. A. J. Organomet. Chem. 1980, 199, 119-135. (m) Almeida, J. F.; Pidcock, A. J. Organomet. Chem. 1981, 209, 415-423. (n) Fujimura, O. J. Am. Chem. Soc. 1998, 120, 10032-10039. Cu: (o) Krüger. J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837-838 and references therein.
38. For a review, see: (a) Mekelburger, H. B.; Wilcox, C. S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: New York, 1991; Vol. 2, pp 99-131 and references therein. For recent selected examples of middle and late transition metal enolate complexes, see the following references. W and Mo: (b) Burkhardt, E. R.; Doney, J. J.; Slough, G. A.; Stack, J. M.; Heathcock, C. H.; Bergman, R. G. Pure Appl. Chem. 1988, 60, 1-6. (c) Faller, J. W.; Ma, Y. Organometallics 1993, 12, 1927-1930. Re: (d) Stack, J. G.; Simpson, R. D.; Hollander, F. J.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1990, 112, 2716-2729. Ru: (e) Rasley, B. T.; Rapta, M.; Kulawiec, R. J. Organometallics 1996, 15, 2852-2854. (f) Hartwig, J. F.; Bergman, R. G.; Andersen, R. A. Organometallics 1991, 10, 3326-3344. Rh and Ir: (g) Milstein, D. J. Am. Chem. Soc. 1982, 104, 5227-5228. (h) Aoyama, Y.; Yoshida, T.; Ogoshi, H. Tetrahedron Lett. 1985, 26, 6107- 6108. (i) Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1989, 111, 938-949. (j) Milstein, D.; Calabrese, J. C. J. Am. Chem. Soc. 1982, 104, 3773-3774. Pt: (k) Cairns, M. A.; Dixon, K. R.; Smith, M. A. R. J. Organomet. Chem. 1977, 135, C33-C34. (l) Arnold, D. P.; Bennett, M. A. J. Organomet. Chem. 1980, 199, 119-135. (m) Almeida, J. F.; Pidcock, A. J. Organomet. Chem. 1981, 209, 415-423. (n) Fujimura, O. J. Am. Chem. Soc. 1998, 120, 10032-10039. Cu: (o) Krüger. J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837-838 and references therein.
39. For a review, see: (a) Mekelburger, H. B.; Wilcox, C. S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: New York, 1991; Vol. 2, pp 99-131 and references therein. For recent selected examples of middle and late transition metal enolate complexes, see the following references. W and Mo: (b) Burkhardt, E. R.; Doney, J. J.; Slough, G. A.; Stack, J. M.; Heathcock, C. H.; Bergman, R. G. Pure Appl. Chem. 1988, 60, 1-6. (c) Faller, J. W.; Ma, Y. Organometallics 1993, 12, 1927-1930. Re: (d) Stack, J. G.; Simpson, R. D.; Hollander, F. J.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1990, 112, 2716-2729. Ru: (e) Rasley, B. T.; Rapta, M.; Kulawiec, R. J. Organometallics 1996, 15, 2852-2854. (f) Hartwig, J. F.; Bergman, R. G.; Andersen, R. A. Organometallics 1991, 10, 3326-3344. Rh and Ir: (g) Milstein, D. J. Am. Chem. Soc. 1982, 104, 5227-5228. (h) Aoyama, Y.; Yoshida, T.; Ogoshi, H. Tetrahedron Lett. 1985, 26, 6107- 6108. (i) Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1989, 111, 938-949. (j) Milstein, D.; Calabrese, J. C. J. Am. Chem. Soc. 1982, 104, 3773-3774. Pt: (k) Cairns, M. A.; Dixon, K. R.; Smith, M. A. R. J. Organomet. Chem. 1977, 135, C33-C34. (l) Arnold, D. P.; Bennett, M. A. J. Organomet. Chem. 1980, 199, 119-135. (m) Almeida, J. F.; Pidcock, A. J. Organomet. Chem. 1981, 209, 415-423. (n) Fujimura, O. J. Am. Chem. Soc. 1998, 120, 10032-10039. Cu: (o) Krüger. J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837-838 and references therein.
40. For a review, see: (a) Mekelburger, H. B.; Wilcox, C. S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: New York, 1991; Vol. 2, pp 99-131 and references therein. For recent selected examples of middle and late transition metal enolate complexes, see the following references. W and Mo: (b) Burkhardt, E. R.; Doney, J. J.; Slough, G. A.; Stack, J. M.; Heathcock, C. H.; Bergman, R. G. Pure Appl. Chem. 1988, 60, 1-6. (c) Faller, J. W.; Ma, Y. Organometallics 1993, 12, 1927-1930. Re: (d) Stack, J. G.; Simpson, R. D.; Hollander, F. J.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1990, 112, 2716-2729. Ru: (e) Rasley, B. T.; Rapta, M.; Kulawiec, R. J. Organometallics 1996, 15, 2852-2854. (f) Hartwig, J. F.; Bergman, R. G.; Andersen, R. A. Organometallics 1991, 10, 3326-3344. Rh and Ir: (g) Milstein, D. J. Am. Chem. Soc. 1982, 104, 5227-5228. (h) Aoyama, Y.; Yoshida, T.; Ogoshi, H. Tetrahedron Lett. 1985, 26, 6107-6108. (i) Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1989, 111, 938-949. (j) Milstein, D.; Calabrese, J. C. J. Am. Chem. Soc. 1982, 104, 3773-3774. Pt: (k) Cairns, M. A.; Dixon, K. R.; Smith, M. A. R. J. Organomet. Chem. 1977, 135, C33-C34. (l) Arnold, D. P.; Bennett, M. A. J. Organomet. Chem. 1980, 199, 119-135. (m) Almeida, J. F.; Pidcock, A. J. Organomet. Chem. 1981, 209, 415-423. (n) Fujimura, O. J. Am. Chem. Soc. 1998, 120, 10032-10039. Cu: (o) Krüger. J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837-838 and references therein.
41. For a review, see: (a) Mekelburger, H. B.; Wilcox, C. S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: New York, 1991; Vol. 2, pp 99-131 and references therein. For recent selected examples of middle and late transition metal enolate complexes, see the following references. W and Mo: (b) Burkhardt, E. R.; Doney, J. J.; Slough, G. A.; Stack, J. M.; Heathcock, C. H.; Bergman, R. G. Pure Appl. Chem. 1988, 60, 1-6. (c) Faller, J. W.; Ma, Y. Organometallics 1993, 12, 1927-1930. Re: (d) Stack, J. G.; Simpson, R. D.; Hollander, F. J.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1990, 112, 2716-2729. Ru: (e) Rasley, B. T.; Rapta, M.; Kulawiec, R. J. Organometallics 1996, 15, 2852-2854. (f) Hartwig, J. F.; Bergman, R. G.; Andersen, R. A. Organometallics 1991, 10, 3326-3344. Rh and Ir: (g) Milstein, D. J. Am. Chem. Soc. 1982, 104, 5227-5228. (h) Aoyama, Y.; Yoshida, T.; Ogoshi, H. Tetrahedron Lett. 1985, 26, 6107- 6108. (i) Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1989, 111, 938-949. (j) Milstein, D.; Calabrese, J. C. J. Am. Chem. Soc. 1982, 104, 3773-3774. Pt: (k) Cairns, M. A.; Dixon, K. R.; Smith, M. A. R. J. Organomet. Chem. 1977, 135, C33-C34. (l) Arnold, D. P.; Bennett, M. A. J. Organomet. Chem. 1980, 199, 119-135. (m) Almeida, J. F.; Pidcock, A. J. Organomet. Chem. 1981, 209, 415-423. (n) Fujimura, O. J. Am. Chem. Soc. 1998, 120, 10032-10039. Cu: (o) Krüger. J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837-838 and references therein.
42. For a review, see: (a) Mekelburger, H. B.; Wilcox, C. S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: New York, 1991; Vol. 2, pp 99-131 and references therein. For recent selected examples of middle and late transition metal enolate complexes, see the following references. W and Mo: (b) Burkhardt, E. R.; Doney, J. J.; Slough, G. A.; Stack, J. M.; Heathcock, C. H.; Bergman, R. G. Pure Appl. Chem. 1988, 60, 1-6. (c) Faller, J. W.; Ma, Y. Organometallics 1993, 12, 1927-1930. Re: (d) Stack, J. G.; Simpson, R. D.; Hollander, F. J.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1990, 112, 2716-2729. Ru: (e) Rasley, B. T.; Rapta, M.; Kulawiec, R. J. Organometallics 1996, 15, 2852-2854. (f) Hartwig, J. F.; Bergman, R. G.; Andersen, R. A. Organometallics 1991, 10, 3326-3344. Rh and Ir: (g) Milstein, D. J. Am. Chem. Soc. 1982, 104, 5227-5228. (h) Aoyama, Y.; Yoshida, T.; Ogoshi, H. Tetrahedron Lett. 1985, 26, 6107- 6108. (i) Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1989, 111, 938-949. (j) Milstein, D.; Calabrese, J. C. J. Am. Chem. Soc. 1982, 104, 3773-3774. Pt: (k) Cairns, M. A.; Dixon, K. R.; Smith, M. A. R. J. Organomet. Chem. 1977, 135, C33-C34. (l) Arnold, D. P.; Bennett, M. A. J. Organomet. Chem. 1980, 199, 119-135. (m) Almeida, J. F.; Pidcock, A. J. Organomet. Chem. 1981, 209, 415-423. (n) Fujimura, O. J. Am. Chem. Soc. 1998, 120, 10032-10039. Cu: (o) Krüger. J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837-838 and references therein.
43. For a review, see: (a) Mekelburger, H. B.; Wilcox, C. S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: New York, 1991; Vol. 2, pp 99-131 and references therein. For recent selected examples of middle and late transition metal enolate complexes, see the following references. W and Mo: (b) Burkhardt, E. R.; Doney, J. J.; Slough, G. A.; Stack, J. M.; Heathcock, C. H.; Bergman, R. G. Pure Appl. Chem. 1988, 60, 1-6. (c) Faller, J. W.; Ma, Y. Organometallics 1993, 12, 1927-1930. Re: (d) Stack, J. G.; Simpson, R. D.; Hollander, F. J.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1990, 112, 2716-2729. Ru: (e) Rasley, B. T.; Rapta, M.; Kulawiec, R. J. Organometallics 1996, 15, 2852-2854. (f) Hartwig, J. F.; Bergman, R. G.; Andersen, R. A. Organometallics 1991, 10, 3326-3344. Rh and Ir: (g) Milstein, D. J. Am. Chem. Soc. 1982, 104, 5227-5228. (h) Aoyama, Y.; Yoshida, T.; Ogoshi, H. Tetrahedron Lett. 1985, 26, 6107- 6108. (i) Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1989, 111, 938-949. (j) Milstein, D.; Calabrese, J. C. J. Am. Chem. Soc. 1982, 104, 3773-3774. Pt: (k) Cairns, M. A.; Dixon, K. R.; Smith, M. A. R. J. Organomet. Chem. 1977, 135, C33-C34. (l) Arnold, D. P.; Bennett, M. A. J. Organomet. Chem. 1980, 199, 119-135. (m) Almeida, J. F.; Pidcock, A. J. Organomet. Chem. 1981, 209, 415-423. (n) Fujimura, O. J. Am. Chem. Soc. 1998, 120, 10032-10039. Cu: (o) Krüger. J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837-838 and references therein.
44. For a review, see: (a) Mekelburger, H. B.; Wilcox, C. S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: New York, 1991; Vol. 2, pp 99-131 and references therein. For recent selected examples of middle and late transition metal enolate complexes, see the following references. W and Mo: (b) Burkhardt, E. R.; Doney, J. J.; Slough, G. A.; Stack, J. M.; Heathcock, C. H.; Bergman, R. G. Pure Appl. Chem. 1988, 60, 1-6. (c) Faller, J. W.; Ma, Y. Organometallics 1993, 12, 1927-1930. Re: (d) Stack, J. G.; Simpson, R. D.; Hollander, F. J.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1990, 112, 2716-2729. Ru: (e) Rasley, B. T.; Rapta, M.; Kulawiec, R. J. Organometallics 1996, 15, 2852-2854. (f) Hartwig, J. F.; Bergman, R. G.; Andersen, R. A. Organometallics 1991, 10, 3326-3344. Rh and Ir: (g) Milstein, D. J. Am. Chem. Soc. 1982, 104, 5227-5228. (h) Aoyama, Y.; Yoshida, T.; Ogoshi, H. Tetrahedron Lett. 1985, 26, 6107- 6108. (i) Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1989, 111, 938-949. (j) Milstein, D.; Calabrese, J. C. J. Am. Chem. Soc. 1982, 104, 3773-3774. Pt: (k) Cairns, M. A.; Dixon, K. R.; Smith, M. A. R. J. Organomet. Chem. 1977, 135, C33-C34. (l) Arnold, D. P.; Bennett, M. A. J. Organomet. Chem. 1980, 199, 119-135. (m) Almeida, J. F.; Pidcock, A. J. Organomet. Chem. 1981, 209, 415-423. (n) Fujimura, O. J. Am. Chem. Soc. 1998, 120, 10032-10039. Cu: (o) Krüger. J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837-838 and references therein.
45. For a review, see: (a) Mekelburger, H. B.; Wilcox, C. S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: New York, 1991; Vol. 2, pp 99-131 and references therein. For recent selected examples of middle and late transition metal enolate complexes, see the following references. W and Mo: (b) Burkhardt, E. R.; Doney, J. J.; Slough, G. A.; Stack, J. M.; Heathcock, C. H.; Bergman, R. G. Pure Appl. Chem. 1988, 60, 1-6. (c) Faller, J. W.; Ma, Y. Organometallics 1993, 12, 1927-1930. Re: (d) Stack, J. G.; Simpson, R. D.; Hollander, F. J.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1990, 112, 2716-2729. Ru: (e) Rasley, B. T.; Rapta, M.; Kulawiec, R. J. Organometallics 1996, 15, 2852-2854. (f) Hartwig, J. F.; Bergman, R. G.; Andersen, R. A. Organometallics 1991, 10, 3326-3344. Rh and Ir: (g) Milstein, D. J. Am. Chem. Soc. 1982, 104, 5227-5228. (h) Aoyama, Y.; Yoshida, T.; Ogoshi, H. Tetrahedron Lett. 1985, 26, 6107- 6108. (i) Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1989, 111, 938-949. (j) Milstein, D.; Calabrese, J. C. J. Am. Chem. Soc. 1982, 104, 3773-3774. Pt: (k) Cairns, M. A.; Dixon, K. R.; Smith, M. A. R. J. Organomet. Chem. 1977, 135, C33-C34. (l) Arnold, D. P.; Bennett, M. A. J. Organomet. Chem. 1980, 199, 119-135. (m) Almeida, J. F.; Pidcock, A. J. Organomet. Chem. 1981, 209, 415-423. (n) Fujimura, O. J. Am. Chem. Soc. 1998, 120, 10032-10039. Cu: (o) Krüger. J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837-838 and references therein.
46. For a review, see: (a) Mekelburger, H. B.; Wilcox, C. S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: New York, 1991; Vol. 2, pp 99-131 and references therein. For recent selected examples of middle and late transition metal enolate complexes, see the following references. W and Mo: (b) Burkhardt, E. R.; Doney, J. J.; Slough, G. A.; Stack, J. M.; Heathcock, C. H.; Bergman, R. G. Pure Appl. Chem. 1988, 60, 1-6. (c) Faller, J. W.; Ma, Y. Organometallics 1993, 12, 1927-1930. Re: (d) Stack, J. G.; Simpson, R. D.; Hollander, F. J.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1990, 112, 2716-2729. Ru: (e) Rasley, B. T.; Rapta, M.; Kulawiec, R. J. Organometallics 1996, 15, 2852-2854. (f) Hartwig, J. F.; Bergman, R. G.; Andersen, R. A. Organometallics 1991, 10, 3326-3344. Rh and Ir: (g) Milstein, D. J. Am. Chem. Soc. 1982, 104, 5227-5228. (h) Aoyama, Y.; Yoshida, T.; Ogoshi, H. Tetrahedron Lett. 1985, 26, 6107- 6108. (i) Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1989, 111, 938-949. (j) Milstein, D.; Calabrese, J. C. J. Am. Chem. Soc. 1982, 104, 3773-3774. Pt: (k) Cairns, M. A.; Dixon, K. R.; Smith, M. A. R. J. Organomet. Chem. 1977, 135, C33-C34. (l) Arnold, D. P.; Bennett, M. A. J. Organomet. Chem. 1980, 199, 119-135. (m) Almeida, J. F.; Pidcock, A. J. Organomet. Chem. 1981, 209, 415-423. (n) Fujimura, O. J. Am. Chem. Soc. 1998, 120, 10032-10039. Cu: (o) Krüger. J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837-838 and references therein.
47. For a review, see: (a) Mekelburger, H. B.; Wilcox, C. S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: New York, 1991; Vol. 2, pp 99-131 and references therein. For recent selected examples of middle and late transition metal enolate complexes, see the following references. W and Mo: (b) Burkhardt, E. R.; Doney, J. J.; Slough, G. A.; Stack, J. M.; Heathcock, C. H.; Bergman, R. G. Pure Appl. Chem. 1988, 60, 1-6. (c) Faller, J. W.; Ma, Y. Organometallics 1993, 12, 1927-1930. Re: (d) Stack, J. G.; Simpson, R. D.; Hollander, F. J.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1990, 112, 2716-2729. Ru: (e) Rasley, B. T.; Rapta, M.; Kulawiec, R. J. Organometallics 1996, 15, 2852-2854. (f) Hartwig, J. F.; Bergman, R. G.; Andersen, R. A. Organometallics 1991, 10, 3326-3344. Rh and Ir: (g) Milstein, D. J. Am. Chem. Soc. 1982, 104, 5227-5228. (h) Aoyama, Y.; Yoshida, T.; Ogoshi, H. Tetrahedron Lett. 1985, 26, 6107- 6108. (i) Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1989, 111, 938-949. (j) Milstein, D.; Calabrese, J. C. J. Am. Chem. Soc. 1982, 104, 3773-3774. Pt: (k) Cairns, M. A.; Dixon, K. R.; Smith, M. A. R. J. Organomet. Chem. 1977, 135, C33-C34. (l) Arnold, D. P.; Bennett, M. A. J. Organomet. Chem. 1980, 199, 119-135. (m) Almeida, J. F.; Pidcock, A. J. Organomet. Chem. 1981, 209, 415-423. (n) Fujimura, O. J. Am. Chem. Soc. 1998, 120, 10032-10039. Cu: (o) Krüger. J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837-838 and references therein.
48. (a) Ito, Y.; Hirano, T.; Saegusa, T. J. Org. Chem. 1978, 43, 1011-1013.
49. (b) Ito, Y.; Aoyama, H.; Hirano, T.; Mochizuki, A.; Saegusa, T. J. Am. Chem. Soc. 1979, 101, 494-496.
50. (c) Tsuji, J.; Mandai, T. Acc. Chem. Res. 1987, 20, 140-145.
51. (d) Nokami, J.; Mandai, T.; Watanabe, H.; Ohyama, H.; Tsuji, J. J. Am. Chem. Soc. 1989, 111, 4126-4127.
52. (e) Nokami, J.; Watanabe, H.; Mandai, T.; Kawada, M.; Tsuji, J. Tetrahedron Lett. 1989, 30, 4829-4832.
53. (f) Masuyama, Y.; Sakai, T.; Kato, T.; Kurusu, Y. Bull. Chem. Soc. Jpn. 1994, 67, 2265-2272.
54. (g) Kuwajima, I.; Urabe, H. J. Am. Chem. Soc. 1982, 104, 6831-6833.
55. (h) Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108-11109.
56. (i) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 12382-12383.
57. (j) Åhman, J.; Wolfe, J. P., Troutman, M. V.; Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 1918-1919.
58. (k) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366-2368 and references therein.
59. (a) Yoshimura, N.; Murahashi, S.-I.; Moritani, I. J. Organomet. Chem. 1973, 52, C58-C60.
60. (b) Ho, Y.; Nakatsuka, M.; Kise, N.; Saegusa, T. Tetrahedron Lett. 1980, 21, 2873-2876.
61. (c) Bertani, R.; Castellani, C. B.; Crociani, B. J. Organomet. Chem. 1984, 269, C15-C18.
62. (d) Wanat, R. A.; Collum, D. B. Organometallics 1986, 5, 120-127.
63. (e) Burkhardt, E. R.; Bergman, R. G.; Heathcock, C. H. Organometallics 1990, 9, 30-44.
64. (f) Veya, P.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Organometallics 1993, 12, 4899-4907.
65. (g) Vicente, J.; Abad, J. A.; Chicote, M. T.; Abrisqueta, M. D. Lorca, J. A.; de Arellano, M. C. R. Organometallics 1998, 17, 1564-1568 and references therein.
66. For a review of hydroxo complexes of transition metals, see: (a) Bryndza, H. E.; Tam, W. Chem. Rev. 1988, 88,.1163-1188 and references therein. For hydroxo palladium complexes, see: (b) Yoshida, T.; Okano, T. Otsuka, S. J. Chem. Soc., Dalton Trans. 1976, 993-999. (c) Grushin, V. V.; Alper, H. Organometallics 1993, 12, 1890-1901. (d) Grushin, V. V.; Alper, H. Organometallics 1996, 15, 5242-5245 and references therein.
67. For a review of hydroxo complexes of transition metals, see: (a) Bryndza, H. E.; Tam, W. Chem. Rev. 1988, 88,.1163-1188 and references therein. For hydroxo palladium complexes, see: (b) Yoshida, T.; Okano, T. Otsuka, S. J. Chem. Soc., Dalton Trans. 1976, 993-999. (c) Grushin, V. V.; Alper, H. Organometallics 1993, 12, 1890-1901. (d) Grushin, V. V.; Alper, H. Organometallics 1996, 15, 5242-5245 and references therein.
68. For a review of hydroxo complexes of transition metals, see: (a) Bryndza, H. E.; Tam, W. Chem. Rev. 1988, 88,.1163-1188 and references therein. For hydroxo palladium complexes, see: (b) Yoshida, T.; Okano, T. Otsuka, S. J. Chem. Soc., Dalton Trans. 1976, 993-999. (c) Grushin, V. V.; Alper, H. Organometallics 1993, 12, 1890-1901. (d) Grushin, V. V.; Alper, H. Organometallics 1996, 15, 5242-5245 and references therein.
69. For a review of hydroxo complexes of transition metals, see: (a) Bryndza, H. E.; Tam, W. Chem. Rev. 1988, 88,.1163-1188 and references therein. For hydroxo palladium complexes, see: (b) Yoshida, T.; Okano, T. Otsuka, S. J. Chem. Soc., Dalton Trans. 1976, 993-999. (c) Grushin, V. V.; Alper, H. Organometallics 1993, 12, 1890-1901. (d) Grushin, V. V.; Alper, H. Organometallics 1996, 15, 5242-5245 and references therein.
70. Fujii, A.; Sodeoka, M., unpublished results.
71. +. This fact indicated that the mononuclear complex 7 was formed in the reaction mixture.
72. (a) Tsutui, M.; Ori, M.; Francis, J. J. Am. Chem. Soc. 1972, 94, 1414-1415.
73. (b) Hillis, J.; Tsutui, M. J. Am. Chem. Soc. 1973, 95, 7907-7908.
74. Tietze, L. F.; Bratz, M. Synthesis 1989, 439-442.
75. Kelly, T. R.; Schmid, T. E.; Haggerty, J. G. Synthesis 1972, 544-545.