Diastereoselectivity in enolate coordination in a new class of chiral ruthenium enolate complexes

Organometallics

Volumn 15, Issue 13, 1996, Pages 2852-2854

  Rasley, Brian T ^a   Rapta, Miroslav ^a   Kulawiec, Robert J ^a  

^a GEORGETOWN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001200566     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om960224j     Document Type: Article

References (43)

1. (a) Additions to C-X π-Bonds, Part 1; Section 1: Uncatalyzed Additions of Nucleophilic Alkenes to C=X. Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, U.K., 1991; Vol. 2.
2. (b) Heathcock, C. H. In Comprehensive Carbanion Chemistry; Buncel, E., Durst, T., Eds.; Elsevier; Amsterdam, 1984; Part B, Chapter 4.
3. (c) Heathcock, C. H. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, Chapter 2.
4. (a) Hegedus, L. S. Transition Metals in the Synthesis of Complex Organic Molecules; University Science Books: Mill Valley, CA, 1994.
5. (b) Davies, S. G. Organotransition Metal Chemistry: Applications to Organic Synthesis; Pergamon Press: Oxford, U.K., 1982.
6. (c) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993.
7. (d) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley-Interscience: New York, 1994.
8. Although no comprehensive review exists, extensive listings of well-characterized transition-metal-enolate complexes are given in the following references:(a) Burkhardt, E. R.; Doney, J. J.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1987, 109, 2022-2039. (b) Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1989, 111, 938-949. For other leading examples, see: (c) 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. (d) Stack, J. G.; Simpson, R. D.; Hollander, F. J.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1990, 112, 2716-2729. (e) Balegroune, F.; Grandjean, D.; Lakkis, D.; Matt, D. J. Chem,. Soc., Chem. Commun. 1992, 1084-1085. (f) Demerseman, B.; Guilbert, B.; Renouard, C.; Gonzalez, M.; Dixneuf, P. H.; Masi, D.; Mealli, C. Organometallics 1993, 12, 3906-3917. (g) Veya, P.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Organometallics 1993, 12, 4899-4907.
9. Although no comprehensive review exists, extensive listings of well-characterized transition-metal-enolate complexes are given in the following references:(a) Burkhardt, E. R.; Doney, J. J.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1987, 109, 2022-2039. (b) Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1989, 111, 938-949. For other leading examples, see: (c) 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. (d) Stack, J. G.; Simpson, R. D.; Hollander, F. J.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1990, 112, 2716-2729. (e) Balegroune, F.; Grandjean, D.; Lakkis, D.; Matt, D. J. Chem,. Soc., Chem. Commun. 1992, 1084-1085. (f) Demerseman, B.; Guilbert, B.; Renouard, C.; Gonzalez, M.; Dixneuf, P. H.; Masi, D.; Mealli, C. Organometallics 1993, 12, 3906-3917. (g) Veya, P.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Organometallics 1993, 12, 4899-4907.
10. Although no comprehensive review exists, extensive listings of well-characterized transition-metal-enolate complexes are given in the following references:(a) Burkhardt, E. R.; Doney, J. J.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1987, 109, 2022-2039. (b) Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1989, 111, 938-949. For other leading examples, see: (c) 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. (d) Stack, J. G.; Simpson, R. D.; Hollander, F. J.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1990, 112, 2716-2729. (e) Balegroune, F.; Grandjean, D.; Lakkis, D.; Matt, D. J. Chem,. Soc., Chem. Commun. 1992, 1084-1085. (f) Demerseman, B.; Guilbert, B.; Renouard, C.; Gonzalez, M.; Dixneuf, P. H.; Masi, D.; Mealli, C. Organometallics 1993, 12, 3906-3917. (g) Veya, P.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Organometallics 1993, 12, 4899-4907.
11. Although no comprehensive review exists, extensive listings of well-characterized transition-metal-enolate complexes are given in the following references:(a) Burkhardt, E. R.; Doney, J. J.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1987, 109, 2022-2039. (b) Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1989, 111, 938-949. For other leading examples, see: (c) 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. (d) Stack, J. G.; Simpson, R. D.; Hollander, F. J.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1990, 112, 2716-2729. (e) Balegroune, F.; Grandjean, D.; Lakkis, D.; Matt, D. J. Chem,. Soc., Chem. Commun. 1992, 1084-1085. (f) Demerseman, B.; Guilbert, B.; Renouard, C.; Gonzalez, M.; Dixneuf, P. H.; Masi, D.; Mealli, C. Organometallics 1993, 12, 3906-3917. (g) Veya, P.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Organometallics 1993, 12, 4899-4907.
12. Although no comprehensive review exists, extensive listings of well-characterized transition-metal-enolate complexes are given in the following references:(a) Burkhardt, E. R.; Doney, J. J.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1987, 109, 2022-2039. (b) Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1989, 111, 938-949. For other leading examples, see: (c) 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. (d) Stack, J. G.; Simpson, R. D.; Hollander, F. J.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1990, 112, 2716-2729. (e) Balegroune, F.; Grandjean, D.; Lakkis, D.; Matt, D. J. Chem,. Soc., Chem. Commun. 1992, 1084-1085. (f) Demerseman, B.; Guilbert, B.; Renouard, C.; Gonzalez, M.; Dixneuf, P. H.; Masi, D.; Mealli, C. Organometallics 1993, 12, 3906-3917. (g) Veya, P.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Organometallics 1993, 12, 4899-4907.
13. Although no comprehensive review exists, extensive listings of well-characterized transition-metal-enolate complexes are given in the following references:(a) Burkhardt, E. R.; Doney, J. J.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1987, 109, 2022-2039. (b) Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1989, 111, 938-949. For other leading examples, see: (c) 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. (d) Stack, J. G.; Simpson, R. D.; Hollander, F. J.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1990, 112, 2716-2729. (e) Balegroune, F.; Grandjean, D.; Lakkis, D.; Matt, D. J. Chem,. Soc., Chem. Commun. 1992, 1084-1085. (f) Demerseman, B.; Guilbert, B.; Renouard, C.; Gonzalez, M.; Dixneuf, P. H.; Masi, D.; Mealli, C. Organometallics 1993, 12, 3906-3917. (g) Veya, P.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Organometallics 1993, 12, 4899-4907.
14. Although no comprehensive review exists, extensive listings of well-characterized transition-metal-enolate complexes are given in the following references:(a) Burkhardt, E. R.; Doney, J. J.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1987, 109, 2022-2039. (b) Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1989, 111, 938-949. For other leading examples, see: (c) 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. (d) Stack, J. G.; Simpson, R. D.; Hollander, F. J.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1990, 112, 2716-2729. (e) Balegroune, F.; Grandjean, D.; Lakkis, D.; Matt, D. J. Chem,. Soc., Chem. Commun. 1992, 1084-1085. (f) Demerseman, B.; Guilbert, B.; Renouard, C.; Gonzalez, M.; Dixneuf, P. H.; Masi, D.; Mealli, C. Organometallics 1993, 12, 3906-3917. (g) Veya, P.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Organometallics 1993, 12, 4899-4907.
15. (a) Hartwig, J. F.; Bergman, R. G.; Andersen, R. A. J. Am. Chem. Soc. 1990, 112, 5670-5671.
16. (b) Hartwig, J. F.; Bergman, R. G.; Andersen, R. A. Organometallics 1991, 10, 3326-3344.
17. For leading examples, see: (a) Ito, Y.; Aoyama, H.; Hirao, T.; Mochizuki, A.; Saegusa, T. J. Am. Chem. Soc. 1979, 101, 494-496. (b) Hirao, T.; Fujihara, Y.; Tsuno, S.; Ohshiro, Y.; Agawa, T. Chem. Lett. 1984, 367-368. (c) Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405-6406. (d) Sato, S.; Matsuda, I.; Izumi, Y. Tetrahedron Lett. 1986, 27, 5517-5520. (e) Reetz, M.; Vougioukas, A. E. Tetrahedron Lett. 1987, 28, 793-796. (f) Naota, T.; Taki, H.; Mizuno, M.; Murahashi, S.-I. J. Am. Chem. Soc. 1989, 111, 5954-5955. (g) Paganelli, S.; Schionato, A.; Botteghi, C. Tetrahedron Lett. 1991, 32, 2807-2810. (h) Paterson, I. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, U.K., 1991; Vol. 2, Chapter 1.9. (i) Toyota, M.; Nishikawa, Y.; Motoki, N.; Yoshida, N.; Fukumoto, K. Tetrahedron Lett. 1993, 34, 6099-6102. (J) Lin, Y.; Zhu, X.; Xiang, M. J. Organomet. Chem. 1993, 448, 215-218. (k) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648-2649.
18. For leading examples, see: (a) Ito, Y.; Aoyama, H.; Hirao, T.; Mochizuki, A.; Saegusa, T. J. Am. Chem. Soc. 1979, 101, 494-496. (b) Hirao, T.; Fujihara, Y.; Tsuno, S.; Ohshiro, Y.; Agawa, T. Chem. Lett. 1984, 367-368. (c) Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405-6406. (d) Sato, S.; Matsuda, I.; Izumi, Y. Tetrahedron Lett. 1986, 27, 5517-5520. (e) Reetz, M.; Vougioukas, A. E. Tetrahedron Lett. 1987, 28, 793-796. (f) Naota, T.; Taki, H.; Mizuno, M.; Murahashi, S.-I. J. Am. Chem. Soc. 1989, 111, 5954-5955. (g) Paganelli, S.; Schionato, A.; Botteghi, C. Tetrahedron Lett. 1991, 32, 2807-2810. (h) Paterson, I. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, U.K., 1991; Vol. 2, Chapter 1.9. (i) Toyota, M.; Nishikawa, Y.; Motoki, N.; Yoshida, N.; Fukumoto, K. Tetrahedron Lett. 1993, 34, 6099-6102. (J) Lin, Y.; Zhu, X.; Xiang, M. J. Organomet. Chem. 1993, 448, 215-218. (k) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648-2649.
19. For leading examples, see: (a) Ito, Y.; Aoyama, H.; Hirao, T.; Mochizuki, A.; Saegusa, T. J. Am. Chem. Soc. 1979, 101, 494-496. (b) Hirao, T.; Fujihara, Y.; Tsuno, S.; Ohshiro, Y.; Agawa, T. Chem. Lett. 1984, 367-368. (c) Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405-6406. (d) Sato, S.; Matsuda, I.; Izumi, Y. Tetrahedron Lett. 1986, 27, 5517-5520. (e) Reetz, M.; Vougioukas, A. E. Tetrahedron Lett. 1987, 28, 793-796. (f) Naota, T.; Taki, H.; Mizuno, M.; Murahashi, S.-I. J. Am. Chem. Soc. 1989, 111, 5954-5955. (g) Paganelli, S.; Schionato, A.; Botteghi, C. Tetrahedron Lett. 1991, 32, 2807-2810. (h) Paterson, I. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, U.K., 1991; Vol. 2, Chapter 1.9. (i) Toyota, M.; Nishikawa, Y.; Motoki, N.; Yoshida, N.; Fukumoto, K. Tetrahedron Lett. 1993, 34, 6099-6102. (J) Lin, Y.; Zhu, X.; Xiang, M. J. Organomet. Chem. 1993, 448, 215-218. (k) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648-2649.
20. For leading examples, see: (a) Ito, Y.; Aoyama, H.; Hirao, T.; Mochizuki, A.; Saegusa, T. J. Am. Chem. Soc. 1979, 101, 494-496. (b) Hirao, T.; Fujihara, Y.; Tsuno, S.; Ohshiro, Y.; Agawa, T. Chem. Lett. 1984, 367-368. (c) Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405-6406. (d) Sato, S.; Matsuda, I.; Izumi, Y. Tetrahedron Lett. 1986, 27, 5517-5520. (e) Reetz, M.; Vougioukas, A. E. Tetrahedron Lett. 1987, 28, 793-796. (f) Naota, T.; Taki, H.; Mizuno, M.; Murahashi, S.-I. J. Am. Chem. Soc. 1989, 111, 5954-5955. (g) Paganelli, S.; Schionato, A.; Botteghi, C. Tetrahedron Lett. 1991, 32, 2807-2810. (h) Paterson, I. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, U.K., 1991; Vol. 2, Chapter 1.9. (i) Toyota, M.; Nishikawa, Y.; Motoki, N.; Yoshida, N.; Fukumoto, K. Tetrahedron Lett. 1993, 34, 6099-6102. (J) Lin, Y.; Zhu, X.; Xiang, M. J. Organomet. Chem. 1993, 448, 215-218. (k) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648-2649.
21. For leading examples, see: (a) Ito, Y.; Aoyama, H.; Hirao, T.; Mochizuki, A.; Saegusa, T. J. Am. Chem. Soc. 1979, 101, 494-496. (b) Hirao, T.; Fujihara, Y.; Tsuno, S.; Ohshiro, Y.; Agawa, T. Chem. Lett. 1984, 367-368. (c) Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405-6406. (d) Sato, S.; Matsuda, I.; Izumi, Y. Tetrahedron Lett. 1986, 27, 5517-5520. (e) Reetz, M.; Vougioukas, A. E. Tetrahedron Lett. 1987, 28, 793-796. (f) Naota, T.; Taki, H.; Mizuno, M.; Murahashi, S.-I. J. Am. Chem. Soc. 1989, 111, 5954-5955. (g) Paganelli, S.; Schionato, A.; Botteghi, C. Tetrahedron Lett. 1991, 32, 2807-2810. (h) Paterson, I. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, U.K., 1991; Vol. 2, Chapter 1.9. (i) Toyota, M.; Nishikawa, Y.; Motoki, N.; Yoshida, N.; Fukumoto, K. Tetrahedron Lett. 1993, 34, 6099-6102. (J) Lin, Y.; Zhu, X.; Xiang, M. J. Organomet. Chem. 1993, 448, 215-218. (k) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648-2649.
22. For leading examples, see: (a) Ito, Y.; Aoyama, H.; Hirao, T.; Mochizuki, A.; Saegusa, T. J. Am. Chem. Soc. 1979, 101, 494-496. (b) Hirao, T.; Fujihara, Y.; Tsuno, S.; Ohshiro, Y.; Agawa, T. Chem. Lett. 1984, 367-368. (c) Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405-6406. (d) Sato, S.; Matsuda, I.; Izumi, Y. Tetrahedron Lett. 1986, 27, 5517-5520. (e) Reetz, M.; Vougioukas, A. E. Tetrahedron Lett. 1987, 28, 793-796. (f) Naota, T.; Taki, H.; Mizuno, M.; Murahashi, S.-I. J. Am. Chem. Soc. 1989, 111, 5954-5955. (g) Paganelli, S.; Schionato, A.; Botteghi, C. Tetrahedron Lett. 1991, 32, 2807-2810. (h) Paterson, I. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, U.K., 1991; Vol. 2, Chapter 1.9. (i) Toyota, M.; Nishikawa, Y.; Motoki, N.; Yoshida, N.; Fukumoto, K. Tetrahedron Lett. 1993, 34, 6099-6102. (J) Lin, Y.; Zhu, X.; Xiang, M. J. Organomet. Chem. 1993, 448, 215-218. (k) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648-2649.
23. For leading examples, see: (a) Ito, Y.; Aoyama, H.; Hirao, T.; Mochizuki, A.; Saegusa, T. J. Am. Chem. Soc. 1979, 101, 494-496. (b) Hirao, T.; Fujihara, Y.; Tsuno, S.; Ohshiro, Y.; Agawa, T. Chem. Lett. 1984, 367-368. (c) Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405-6406. (d) Sato, S.; Matsuda, I.; Izumi, Y. Tetrahedron Lett. 1986, 27, 5517-5520. (e) Reetz, M.; Vougioukas, A. E. Tetrahedron Lett. 1987, 28, 793-796. (f) Naota, T.; Taki, H.; Mizuno, M.; Murahashi, S.-I. J. Am. Chem. Soc. 1989, 111, 5954-5955. (g) Paganelli, S.; Schionato, A.; Botteghi, C. Tetrahedron Lett. 1991, 32, 2807-2810. (h) Paterson, I. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, U.K., 1991; Vol. 2, Chapter 1.9. (i) Toyota, M.; Nishikawa, Y.; Motoki, N.; Yoshida, N.; Fukumoto, K. Tetrahedron Lett. 1993, 34, 6099-6102. (J) Lin, Y.; Zhu, X.; Xiang, M. J. Organomet. Chem. 1993, 448, 215-218. (k) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648-2649.
24. For leading examples, see: (a) Ito, Y.; Aoyama, H.; Hirao, T.; Mochizuki, A.; Saegusa, T. J. Am. Chem. Soc. 1979, 101, 494-496. (b) Hirao, T.; Fujihara, Y.; Tsuno, S.; Ohshiro, Y.; Agawa, T. Chem. Lett. 1984, 367-368. (c) Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405-6406. (d) Sato, S.; Matsuda, I.; Izumi, Y. Tetrahedron Lett. 1986, 27, 5517-5520. (e) Reetz, M.; Vougioukas, A. E. Tetrahedron Lett. 1987, 28, 793-796. (f) Naota, T.; Taki, H.; Mizuno, M.; Murahashi, S.-I. J. Am. Chem. Soc. 1989, 111, 5954-5955. (g) Paganelli, S.; Schionato, A.; Botteghi, C. Tetrahedron Lett. 1991, 32, 2807-2810. (h) Paterson, I. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, U.K., 1991; Vol. 2, Chapter 1.9. (i) Toyota, M.; Nishikawa, Y.; Motoki, N.; Yoshida, N.; Fukumoto, K. Tetrahedron Lett. 1993, 34, 6099-6102. (J) Lin, Y.; Zhu, X.; Xiang, M. J. Organomet. Chem. 1993, 448, 215-218. (k) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648-2649.
25. For leading examples, see: (a) Ito, Y.; Aoyama, H.; Hirao, T.; Mochizuki, A.; Saegusa, T. J. Am. Chem. Soc. 1979, 101, 494-496. (b) Hirao, T.; Fujihara, Y.; Tsuno, S.; Ohshiro, Y.; Agawa, T. Chem. Lett. 1984, 367-368. (c) Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405-6406. (d) Sato, S.; Matsuda, I.; Izumi, Y. Tetrahedron Lett. 1986, 27, 5517-5520. (e) Reetz, M.; Vougioukas, A. E. Tetrahedron Lett. 1987, 28, 793-796. (f) Naota, T.; Taki, H.; Mizuno, M.; Murahashi, S.-I. J. Am. Chem. Soc. 1989, 111, 5954-5955. (g) Paganelli, S.; Schionato, A.; Botteghi, C. Tetrahedron Lett. 1991, 32, 2807-2810. (h) Paterson, I. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, U.K., 1991; Vol. 2, Chapter 1.9. (i) Toyota, M.; Nishikawa, Y.; Motoki, N.; Yoshida, N.; Fukumoto, K. Tetrahedron Lett. 1993, 34, 6099-6102. (J) Lin, Y.; Zhu, X.; Xiang, M. J. Organomet. Chem. 1993, 448, 215-218. (k) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648-2649.
26. For leading examples, see: (a) Ito, Y.; Aoyama, H.; Hirao, T.; Mochizuki, A.; Saegusa, T. J. Am. Chem. Soc. 1979, 101, 494-496. (b) Hirao, T.; Fujihara, Y.; Tsuno, S.; Ohshiro, Y.; Agawa, T. Chem. Lett. 1984, 367-368. (c) Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405-6406. (d) Sato, S.; Matsuda, I.; Izumi, Y. Tetrahedron Lett. 1986, 27, 5517-5520. (e) Reetz, M.; Vougioukas, A. E. Tetrahedron Lett. 1987, 28, 793-796. (f) Naota, T.; Taki, H.; Mizuno, M.; Murahashi, S.-I. J. Am. Chem. Soc. 1989, 111, 5954-5955. (g) Paganelli, S.; Schionato, A.; Botteghi, C. Tetrahedron Lett. 1991, 32, 2807-2810. (h) Paterson, I. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, U.K., 1991; Vol. 2, Chapter 1.9. (i) Toyota, M.; Nishikawa, Y.; Motoki, N.; Yoshida, N.; Fukumoto, K. Tetrahedron Lett. 1993, 34, 6099-6102. (J) Lin, Y.; Zhu, X.; Xiang, M. J. Organomet. Chem. 1993, 448, 215-218. (k) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648-2649.
27. For leading examples, see: (a) Ito, Y.; Aoyama, H.; Hirao, T.; Mochizuki, A.; Saegusa, T. J. Am. Chem. Soc. 1979, 101, 494-496. (b) Hirao, T.; Fujihara, Y.; Tsuno, S.; Ohshiro, Y.; Agawa, T. Chem. Lett. 1984, 367-368. (c) Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405-6406. (d) Sato, S.; Matsuda, I.; Izumi, Y. Tetrahedron Lett. 1986, 27, 5517-5520. (e) Reetz, M.; Vougioukas, A. E. Tetrahedron Lett. 1987, 28, 793-796. (f) Naota, T.; Taki, H.; Mizuno, M.; Murahashi, S.-I. J. Am. Chem. Soc. 1989, 111, 5954-5955. (g) Paganelli, S.; Schionato, A.; Botteghi, C. Tetrahedron Lett. 1991, 32, 2807-2810. (h) Paterson, I. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, U.K., 1991; Vol. 2, Chapter 1.9. (i) Toyota, M.; Nishikawa, Y.; Motoki, N.; Yoshida, N.; Fukumoto, K. Tetrahedron Lett. 1993, 34, 6099-6102. (J) Lin, Y.; Zhu, X.; Xiang, M. J. Organomet. Chem. 1993, 448, 215-218. (k) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648-2649.
28. Part of this work has been communicated: Rasley, B. T.; Rapta, M.; Dickman, M. H.; Kulawiec, R. J. Abstracts of Papers, 210th National Meeting of the American Chemical Society, Chicago, IL; American Chemical Society: Washington, DC, 1995; INOR 0305.
29. (a) Albers, M. O.; Robinson, D. J.; Singleton, E. Coord. Chem. Rev. 1987, 79, 1-96.
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31. (c) Davies, S. G.; McNally, J. P.; Smallridge, A. J. Adv. Organomet. Chem. 1990, 30, 1-76.
32. 3), see: Schiemenz, G. P.; Kaack, H. Justus Liebigs Ann. Chem. 1973, 1480-1493, 1494-1504.
33. For the synthesis and crystallographic characterization of 2b, see: Rasley, B. T.; Rapta, M.; Kulawiec, R. J. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1995, C51, 523-525.
34. Complete spectroscopic and analytical data for all new compounds are provided in the Supporting Information.
35. -1, T = 293(2) K, λ = 0.710 73 Å, R = 0.0636 for 6598 reflections with I > 2σ(I).
36. 3) and δ 3.39 (dq, J = 4.0, 5.9 Hz, CH) for the minor diastereomer.
37. -1, T = 293(2) K, λ = 0.710 73 Å, R = 0.0626 for 5155 reflections with I > 2σ(I). See the Supporting Information for details on data collection and structure determination.
38. 3) affords a methyl enol ether complex which exists in the Z configuration, by NOE difference spectroscopy; the O-alkylation is presumed to occur with retention of double-bond geometry: Rasley, B. T. Unpublished results, 1996.
39. (a) Caine, D. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, U.K., 1991; Vol. 3, Chapter 1.1, pp 3-4.
40. (b) Smith, M. B. Organic Synthesis; McGraw-Hill: New York, 1994; pp 880-882.
41. (c) Carey, F. A.; Sundberg, R. G. Advanced Organic Chemistry, Part B: Reactions and Synthesis, 3rd ed.; Plenum: New York, 1990; p 23.
42. 1/2 = 130 h).
43. -1. For examples of enol ether complexes, see: Cutler, A. R.; Raghu, S.; Rosenblum, M. J. Organomet. Chem. 1974, 77, 381-391 and references therein.