Catalytic asymmetric [4+1] cycloaddition of vinylallenes with carbon monoxide: Reversal of the induced chirality by the choice of metal

Journal of the American Chemical Society

Volumn 121, Issue 17, 1999, Pages 4130-4135

  Murakami, Masahiro ^a   Itami, Kenichiro ^a   Ito, Yoshihiko ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON MONOXIDE; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0033526381     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9839365     Document Type: Article

References (48)

1. Colquhoun, H. M.; Thompson, D. J.; Twigg, M. V. Carbonylation: Direct Synthesis of Carbonyl Compounds; Plenum: New York, 1991.
2. (a) Consiglio, G. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; pp 273-302.
3. (b) Agbossou, F.; Carpenter, J.-F.; Mortreux, A. Chem. Rev. 1995, 95, 2485.
4. (c) Gladiali, S.; Bayn, J. C.; Claver, C. Tetrahedron Asymm. 1995, 6, 1453.
5. Hydroformylation: (a) Sakai, N.; Mano, S.; Nozaki, K.; Takaya, H. J. Am. Chem. Soc. 1993, 115, 7033. (b) Sperrle, M.; Consiglio, G. J. Am. Chem. Soc. 1995, 117, 12130. (c) Horiuchi, T.; Ohta, T.; Nozaki, K.; Takaya, H. Chem. Commun. 1996, 155. Alternating carbonylative copolymerization: (d) Brookhardt, M.; Wagner, M. I.; Balavoine, G. G. A.; Haddou, H. A. J. Am. Chem. Soc. 1994, 116, 3641. (e) Bronco, S.; Consiglio, G.; Hutter, R.; Batistini, A.; Suter, U. W. Macromolecules 1994, 27, 4436. (f) Jiang, Z.; Sen, A. J. Am. Chem. Soc. 1995, 117, 4455. (g) Nozaki, K.; Sato, N.; Takaya, H. J. Am. Chem. Soc. 1995, 117, 9911. (h) Nozaki, K.; Sato, N.; Tonomura, Y.; Yasutomi, M.; Takaya, H.; Hiyama, T.; Matsubara, T.; Koga, N. J. Am. Chem. Soc. 1997, 119, 12779.
6. Hydroformylation: (a) Sakai, N.; Mano, S.; Nozaki, K.; Takaya, H. J. Am. Chem. Soc. 1993, 115, 7033. (b) Sperrle, M.; Consiglio, G. J. Am. Chem. Soc. 1995, 117, 12130. (c) Horiuchi, T.; Ohta, T.; Nozaki, K.; Takaya, H. Chem. Commun. 1996, 155. Alternating carbonylative copolymerization: (d) Brookhardt, M.; Wagner, M. I.; Balavoine, G. G. A.; Haddou, H. A. J. Am. Chem. Soc. 1994, 116, 3641. (e) Bronco, S.; Consiglio, G.; Hutter, R.; Batistini, A.; Suter, U. W. Macromolecules 1994, 27, 4436. (f) Jiang, Z.; Sen, A. J. Am. Chem. Soc. 1995, 117, 4455. (g) Nozaki, K.; Sato, N.; Takaya, H. J. Am. Chem. Soc. 1995, 117, 9911. (h) Nozaki, K.; Sato, N.; Tonomura, Y.; Yasutomi, M.; Takaya, H.; Hiyama, T.; Matsubara, T.; Koga, N. J. Am. Chem. Soc. 1997, 119, 12779.
7. Hydroformylation: (a) Sakai, N.; Mano, S.; Nozaki, K.; Takaya, H. J. Am. Chem. Soc. 1993, 115, 7033. (b) Sperrle, M.; Consiglio, G. J. Am. Chem. Soc. 1995, 117, 12130. (c) Horiuchi, T.; Ohta, T.; Nozaki, K.; Takaya, H. Chem. Commun. 1996, 155. Alternating carbonylative copolymerization: (d) Brookhardt, M.; Wagner, M. I.; Balavoine, G. G. A.; Haddou, H. A. J. Am. Chem. Soc. 1994, 116, 3641. (e) Bronco, S.; Consiglio, G.; Hutter, R.; Batistini, A.; Suter, U. W. Macromolecules 1994, 27, 4436. (f) Jiang, Z.; Sen, A. J. Am. Chem. Soc. 1995, 117, 4455. (g) Nozaki, K.; Sato, N.; Takaya, H. J. Am. Chem. Soc. 1995, 117, 9911. (h) Nozaki, K.; Sato, N.; Tonomura, Y.; Yasutomi, M.; Takaya, H.; Hiyama, T.; Matsubara, T.; Koga, N. J. Am. Chem. Soc. 1997, 119, 12779.
8. Hydroformylation: (a) Sakai, N.; Mano, S.; Nozaki, K.; Takaya, H. J. Am. Chem. Soc. 1993, 115, 7033. (b) Sperrle, M.; Consiglio, G. J. Am. Chem. Soc. 1995, 117, 12130. (c) Horiuchi, T.; Ohta, T.; Nozaki, K.; Takaya, H. Chem. Commun. 1996, 155. Alternating carbonylative copolymerization: (d) Brookhardt, M.; Wagner, M. I.; Balavoine, G. G. A.; Haddou, H. A. J. Am. Chem. Soc. 1994, 116, 3641. (e) Bronco, S.; Consiglio, G.; Hutter, R.; Batistini, A.; Suter, U. W. Macromolecules 1994, 27, 4436. (f) Jiang, Z.; Sen, A. J. Am. Chem. Soc. 1995, 117, 4455. (g) Nozaki, K.; Sato, N.; Takaya, H. J. Am. Chem. Soc. 1995, 117, 9911. (h) Nozaki, K.; Sato, N.; Tonomura, Y.; Yasutomi, M.; Takaya, H.; Hiyama, T.; Matsubara, T.; Koga, N. J. Am. Chem. Soc. 1997, 119, 12779.
9. Hydroformylation: (a) Sakai, N.; Mano, S.; Nozaki, K.; Takaya, H. J. Am. Chem. Soc. 1993, 115, 7033. (b) Sperrle, M.; Consiglio, G. J. Am. Chem. Soc. 1995, 117, 12130. (c) Horiuchi, T.; Ohta, T.; Nozaki, K.; Takaya, H. Chem. Commun. 1996, 155. Alternating carbonylative copolymerization: (d) Brookhardt, M.; Wagner, M. I.; Balavoine, G. G. A.; Haddou, H. A. J. Am. Chem. Soc. 1994, 116, 3641. (e) Bronco, S.; Consiglio, G.; Hutter, R.; Batistini, A.; Suter, U. W. Macromolecules 1994, 27, 4436. (f) Jiang, Z.; Sen, A. J. Am. Chem. Soc. 1995, 117, 4455. (g) Nozaki, K.; Sato, N.; Takaya, H. J. Am. Chem. Soc. 1995, 117, 9911. (h) Nozaki, K.; Sato, N.; Tonomura, Y.; Yasutomi, M.; Takaya, H.; Hiyama, T.; Matsubara, T.; Koga, N. J. Am. Chem. Soc. 1997, 119, 12779.
10. Hydroformylation: (a) Sakai, N.; Mano, S.; Nozaki, K.; Takaya, H. J. Am. Chem. Soc. 1993, 115, 7033. (b) Sperrle, M.; Consiglio, G. J. Am. Chem. Soc. 1995, 117, 12130. (c) Horiuchi, T.; Ohta, T.; Nozaki, K.; Takaya, H. Chem. Commun. 1996, 155. Alternating carbonylative copolymerization: (d) Brookhardt, M.; Wagner, M. I.; Balavoine, G. G. A.; Haddou, H. A. J. Am. Chem. Soc. 1994, 116, 3641. (e) Bronco, S.; Consiglio, G.; Hutter, R.; Batistini, A.; Suter, U. W. Macromolecules 1994, 27, 4436. (f) Jiang, Z.; Sen, A. J. Am. Chem. Soc. 1995, 117, 4455. (g) Nozaki, K.; Sato, N.; Takaya, H. J. Am. Chem. Soc. 1995, 117, 9911. (h) Nozaki, K.; Sato, N.; Tonomura, Y.; Yasutomi, M.; Takaya, H.; Hiyama, T.; Matsubara, T.; Koga, N. J. Am. Chem. Soc. 1997, 119, 12779.
11. Hydroformylation: (a) Sakai, N.; Mano, S.; Nozaki, K.; Takaya, H. J. Am. Chem. Soc. 1993, 115, 7033. (b) Sperrle, M.; Consiglio, G. J. Am. Chem. Soc. 1995, 117, 12130. (c) Horiuchi, T.; Ohta, T.; Nozaki, K.; Takaya, H. Chem. Commun. 1996, 155. Alternating carbonylative copolymerization: (d) Brookhardt, M.; Wagner, M. I.; Balavoine, G. G. A.; Haddou, H. A. J. Am. Chem. Soc. 1994, 116, 3641. (e) Bronco, S.; Consiglio, G.; Hutter, R.; Batistini, A.; Suter, U. W. Macromolecules 1994, 27, 4436. (f) Jiang, Z.; Sen, A. J. Am. Chem. Soc. 1995, 117, 4455. (g) Nozaki, K.; Sato, N.; Takaya, H. J. Am. Chem. Soc. 1995, 117, 9911. (h) Nozaki, K.; Sato, N.; Tonomura, Y.; Yasutomi, M.; Takaya, H.; Hiyama, T.; Matsubara, T.; Koga, N. J. Am. Chem. Soc. 1997, 119, 12779.
12. Hydroformylation: (a) Sakai, N.; Mano, S.; Nozaki, K.; Takaya, H. J. Am. Chem. Soc. 1993, 115, 7033. (b) Sperrle, M.; Consiglio, G. J. Am. Chem. Soc. 1995, 117, 12130. (c) Horiuchi, T.; Ohta, T.; Nozaki, K.; Takaya, H. Chem. Commun. 1996, 155. Alternating carbonylative copolymerization: (d) Brookhardt, M.; Wagner, M. I.; Balavoine, G. G. A.; Haddou, H. A. J. Am. Chem. Soc. 1994, 116, 3641. (e) Bronco, S.; Consiglio, G.; Hutter, R.; Batistini, A.; Suter, U. W. Macromolecules 1994, 27, 4436. (f) Jiang, Z.; Sen, A. J. Am. Chem. Soc. 1995, 117, 4455. (g) Nozaki, K.; Sato, N.; Takaya, H. J. Am. Chem. Soc. 1995, 117, 9911. (h) Nozaki, K.; Sato, N.; Tonomura, Y.; Yasutomi, M.; Takaya, H.; Hiyama, T.; Matsubara, T.; Koga, N. J. Am. Chem. Soc. 1997, 119, 12779.
13. (a) Murakami, M.; Itami, K.; Ito, Y. Angew. Chem., Int. Ed. Engl. 1995, 34, 2691.
14. (b) Murakami, M.; Itami, K.; Ito, Y. J. Am. Chem. Soc. 1996, 118, 11672.
15. (c) Murakami, M.; Itami, K.; Ito, Y. Organometallics 1999, 18, 1326.
16. For other examples of transition metal-catalyzed [4 + 1] cycloaddition of vinylallenes, see; (a) Eaton, B. E.; Rollman, B.; Kaduk, J. A. J. Am. Chem. Soc. 1992, 114, 6245. (b) Mandai, T.; Tsuji, J.; Tsujiguchi, Y.; Saito, S. J. Am. Chem. Soc. 1993, 115, 5865. (c) Sigman, M. S.; Eaton, B. E. J. Am. Chem. Soc. 1996, 118, 11783. (d) Darcel, C.; Bruneau, C.; Dixneuf, P. H. Synlett 1996, 218.
17. For other examples of transition metal-catalyzed [4 + 1] cycloaddition of vinylallenes, see; (a) Eaton, B. E.; Rollman, B.; Kaduk, J. A. J. Am. Chem. Soc. 1992, 114, 6245. (b) Mandai, T.; Tsuji, J.; Tsujiguchi, Y.; Saito, S. J. Am. Chem. Soc. 1993, 115, 5865. (c) Sigman, M. S.; Eaton, B. E. J. Am. Chem. Soc. 1996, 118, 11783. (d) Darcel, C.; Bruneau, C.; Dixneuf, P. H. Synlett 1996, 218.
18. For other examples of transition metal-catalyzed [4 + 1] cycloaddition of vinylallenes, see; (a) Eaton, B. E.; Rollman, B.; Kaduk, J. A. J. Am. Chem. Soc. 1992, 114, 6245. (b) Mandai, T.; Tsuji, J.; Tsujiguchi, Y.; Saito, S. J. Am. Chem. Soc. 1993, 115, 5865. (c) Sigman, M. S.; Eaton, B. E. J. Am. Chem. Soc. 1996, 118, 11783. (d) Darcel, C.; Bruneau, C.; Dixneuf, P. H. Synlett 1996, 218.
19. For other examples of transition metal-catalyzed [4 + 1] cycloaddition of vinylallenes, see; (a) Eaton, B. E.; Rollman, B.; Kaduk, J. A. J. Am. Chem. Soc. 1992, 114, 6245. (b) Mandai, T.; Tsuji, J.; Tsujiguchi, Y.; Saito, S. J. Am. Chem. Soc. 1993, 115, 5865. (c) Sigman, M. S.; Eaton, B. E. J. Am. Chem. Soc. 1996, 118, 11783. (d) Darcel, C.; Bruneau, C.; Dixneuf, P. H. Synlett 1996, 218.
20. Preliminary communication: Murakami, M.; Itami, K.; Ito, Y. J. Am. Chem. Soc. 1997, 119, 2950.
21. For asymmetric reactions based on DuPHOS, see: (a) Burk, M. J.; Nugent, W. A.; Harlow, R. L. J. Am. Chem. Soc. 1993, 115, 10125. (b) Burk, M. J.; Kalberg, C. S.; Pizzano, A. J. Am. Chem. Soc. 1998, 120, 4345 and references therein.
22. For asymmetric reactions based on DuPHOS, see: (a) Burk, M. J.; Nugent, W. A.; Harlow, R. L. J. Am. Chem. Soc. 1993, 115, 10125. (b) Burk, M. J.; Kalberg, C. S.; Pizzano, A. J. Am. Chem. Soc. 1998, 120, 4345 and references therein.
23. No [4 + 1] cycloadduct potentially arising from 3 was detected, suggesting the superior reactivity of a vinylallene skeleton.
24. For leading examples, see: (a) Jacobsen, E. N.; Markó, I.; Mungall, W. S.; Schröder, G.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 1968. (b) Hayashi, T.; Matsumoto, Y.; Ito, Y. J. Am. Chem. Soc. 1989, 111, 3426. (c) Zhang, W.; Loeback, J. L.; Wilson, S. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1990, 112, 2801. (d) Uozumi, Y.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 9887. (e) Ohta, T.; Ikegami, H.; Miyake, T.; Takaya, H. J. Organomet. Chem. 1995, 502, 169. (f) Kondakov, D. Y.; Negishi, E. J. Am. Chem. Soc. 1995, 117, 10771.
25. For leading examples, see: (a) Jacobsen, E. N.; Markó, I.; Mungall, W. S.; Schröder, G.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 1968. (b) Hayashi, T.; Matsumoto, Y.; Ito, Y. J. Am. Chem. Soc. 1989, 111, 3426. (c) Zhang, W.; Loeback, J. L.; Wilson, S. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1990, 112, 2801. (d) Uozumi, Y.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 9887. (e) Ohta, T.; Ikegami, H.; Miyake, T.; Takaya, H. J. Organomet. Chem. 1995, 502, 169. (f) Kondakov, D. Y.; Negishi, E. J. Am. Chem. Soc. 1995, 117, 10771.
26. For leading examples, see: (a) Jacobsen, E. N.; Markó, I.; Mungall, W. S.; Schröder, G.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 1968. (b) Hayashi, T.; Matsumoto, Y.; Ito, Y. J. Am. Chem. Soc. 1989, 111, 3426. (c) Zhang, W.; Loeback, J. L.; Wilson, S. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1990, 112, 2801. (d) Uozumi, Y.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 9887. (e) Ohta, T.; Ikegami, H.; Miyake, T.; Takaya, H. J. Organomet. Chem. 1995, 502, 169. (f) Kondakov, D. Y.; Negishi, E. J. Am. Chem. Soc. 1995, 117, 10771.
27. For leading examples, see: (a) Jacobsen, E. N.; Markó, I.; Mungall, W. S.; Schröder, G.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 1968. (b) Hayashi, T.; Matsumoto, Y.; Ito, Y. J. Am. Chem. Soc. 1989, 111, 3426. (c) Zhang, W.; Loeback, J. L.; Wilson, S. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1990, 112, 2801. (d) Uozumi, Y.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 9887. (e) Ohta, T.; Ikegami, H.; Miyake, T.; Takaya, H. J. Organomet. Chem. 1995, 502, 169. (f) Kondakov, D. Y.; Negishi, E. J. Am. Chem. Soc. 1995, 117, 10771.
28. For leading examples, see: (a) Jacobsen, E. N.; Markó, I.; Mungall, W. S.; Schröder, G.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 1968. (b) Hayashi, T.; Matsumoto, Y.; Ito, Y. J. Am. Chem. Soc. 1989, 111, 3426. (c) Zhang, W.; Loeback, J. L.; Wilson, S. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1990, 112, 2801. (d) Uozumi, Y.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 9887. (e) Ohta, T.; Ikegami, H.; Miyake, T.; Takaya, H. J. Organomet. Chem. 1995, 502, 169. (f) Kondakov, D. Y.; Negishi, E. J. Am. Chem. Soc. 1995, 117, 10771.
29. For leading examples, see: (a) Jacobsen, E. N.; Markó, I.; Mungall, W. S.; Schröder, G.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 1968. (b) Hayashi, T.; Matsumoto, Y.; Ito, Y. J. Am. Chem. Soc. 1989, 111, 3426. (c) Zhang, W.; Loeback, J. L.; Wilson, S. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1990, 112, 2801. (d) Uozumi, Y.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 9887. (e) Ohta, T.; Ikegami, H.; Miyake, T.; Takaya, H. J. Organomet. Chem. 1995, 502, 169. (f) Kondakov, D. Y.; Negishi, E. J. Am. Chem. Soc. 1995, 117, 10771.
30. Gemal, A. L.; Luche, J.-L. J. Am. Chem. Soc. 1981, 103, 5454.
31. The cyclopentenones (5) were prone to racemization, probably due to the presence of the phenyl substituent, when subjected to chromatographic isolation.
32. For reversal of the induced chirality by the employed metal, see: (a) Kawano, H.; Ikariya, T.; Ishii, Y.; Saburi, M.; Yoshikawa, S.; Uchida, Y.; Kumobayashi, H. J. Chem. Soc., Perkin Trans. 1 1989, 1571. (b) Kitamura, M.; Hsiao, Y.; Ohta, M.; Tsukamoto, M.; Ohta, T.; Takaya, H.; Noyori, R. J. Org. Chem. 1994, 59, 297. (c) Kinting, A.; Kreuzfeld, H.-J.; Abicht, H.-P. J. Organomet. Chem. 1989, 370, 343. (d) Faller, J. W.; Chase, K. J. Organometallics 1994, 13, 989. (e) Nishibayashi, Y.; Segawa, K.; Ohe, K.; Uemura, S. Organometallics 1995, 14, 5486.
33. For reversal of the induced chirality by the employed metal, see: (a) Kawano, H.; Ikariya, T.; Ishii, Y.; Saburi, M.; Yoshikawa, S.; Uchida, Y.; Kumobayashi, H. J. Chem. Soc., Perkin Trans. 1 1989, 1571. (b) Kitamura, M.; Hsiao, Y.; Ohta, M.; Tsukamoto, M.; Ohta, T.; Takaya, H.; Noyori, R. J. Org. Chem. 1994, 59, 297. (c) Kinting, A.; Kreuzfeld, H.-J.; Abicht, H.-P. J. Organomet. Chem. 1989, 370, 343. (d) Faller, J. W.; Chase, K. J. Organometallics 1994, 13, 989. (e) Nishibayashi, Y.; Segawa, K.; Ohe, K.; Uemura, S. Organometallics 1995, 14, 5486.
34. For reversal of the induced chirality by the employed metal, see: (a) Kawano, H.; Ikariya, T.; Ishii, Y.; Saburi, M.; Yoshikawa, S.; Uchida, Y.; Kumobayashi, H. J. Chem. Soc., Perkin Trans. 1 1989, 1571. (b) Kitamura, M.; Hsiao, Y.; Ohta, M.; Tsukamoto, M.; Ohta, T.; Takaya, H.; Noyori, R. J. Org. Chem. 1994, 59, 297. (c) Kinting, A.; Kreuzfeld, H.-J.; Abicht, H.-P. J. Organomet. Chem. 1989, 370, 343. (d) Faller, J. W.; Chase, K. J. Organometallics 1994, 13, 989. (e) Nishibayashi, Y.; Segawa, K.; Ohe, K.; Uemura, S. Organometallics 1995, 14, 5486.
35. For reversal of the induced chirality by the employed metal, see: (a) Kawano, H.; Ikariya, T.; Ishii, Y.; Saburi, M.; Yoshikawa, S.; Uchida, Y.; Kumobayashi, H. J. Chem. Soc., Perkin Trans. 1 1989, 1571. (b) Kitamura, M.; Hsiao, Y.; Ohta, M.; Tsukamoto, M.; Ohta, T.; Takaya, H.; Noyori, R. J. Org. Chem. 1994, 59, 297. (c) Kinting, A.; Kreuzfeld, H.-J.; Abicht, H.-P. J. Organomet. Chem. 1989, 370, 343. (d) Faller, J. W.; Chase, K. J. Organometallics 1994, 13, 989. (e) Nishibayashi, Y.; Segawa, K.; Ohe, K.; Uemura, S. Organometallics 1995, 14, 5486.
36. For reversal of the induced chirality by the employed metal, see: (a) Kawano, H.; Ikariya, T.; Ishii, Y.; Saburi, M.; Yoshikawa, S.; Uchida, Y.; Kumobayashi, H. J. Chem. Soc., Perkin Trans. 1 1989, 1571. (b) Kitamura, M.; Hsiao, Y.; Ohta, M.; Tsukamoto, M.; Ohta, T.; Takaya, H.; Noyori, R. J. Org. Chem. 1994, 59, 297. (c) Kinting, A.; Kreuzfeld, H.-J.; Abicht, H.-P. J. Organomet. Chem. 1989, 370, 343. (d) Faller, J. W.; Chase, K. J. Organometallics 1994, 13, 989. (e) Nishibayashi, Y.; Segawa, K.; Ohe, K.; Uemura, S. Organometallics 1995, 14, 5486.
37. For reversal of the induced chirality by the presence of an additive, see: (a) Kobayashi, S.; Ishitani, H.; Hachiya, I.; Araki, M. Tetrahedron 1994, 50, 11623. (b) Desimoni, G.; Faita, G.; Invernizzi, A. G.; Righetti, P. Tetrahedron 1997, 53, 7671. (c) Ashimori, A.; Bachand, B.; Overman, L. E.; Poon, D. J. J. Am. Chem. Soc. 1998, 120, 6477.
38. For reversal of the induced chirality by the presence of an additive, see: (a) Kobayashi, S.; Ishitani, H.; Hachiya, I.; Araki, M. Tetrahedron 1994, 50, 11623. (b) Desimoni, G.; Faita, G.; Invernizzi, A. G.; Righetti, P. Tetrahedron 1997, 53, 7671. (c) Ashimori, A.; Bachand, B.; Overman, L. E.; Poon, D. J. J. Am. Chem. Soc. 1998, 120, 6477.
39. For reversal of the induced chirality by the presence of an additive, see: (a) Kobayashi, S.; Ishitani, H.; Hachiya, I.; Araki, M. Tetrahedron 1994, 50, 11623. (b) Desimoni, G.; Faita, G.; Invernizzi, A. G.; Righetti, P. Tetrahedron 1997, 53, 7671. (c) Ashimori, A.; Bachand, B.; Overman, L. E.; Poon, D. J. J. Am. Chem. Soc. 1998, 120, 6477.
40. For reversal of the induced chirality by the dihydrogen pressure, see: Kuwano, R. Doctor Dissertation, Kyoto University, 1998, Chapter 2.
41. Since the formation of 3 could not be avoided even at higher CO pressure (15 atm), it is likely that the thermal ene reaction preferentially occurred with 7. See: Bond, D. J. Org. Chem. Soc. 1990, 55, 661 and references therein.
42. Landis, C. R.; Halpern, J. J. Am. Chem. Soc. 1987, 109, 1746.
43. For an exception, see: Zhang, W.; Lee, N. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 116, 425.
44. Trost, B. M.; Belletire, J. L.; Godleski, S.; Baldwin, J. J.; Christy, M. E.; Ponticello, G. S. J. Org. Chem. 1986, 51, 2370.
45. (a) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49.
46. (b) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
47. 4c
48. Green, M.; Kuc, T. A.; Taylor, S. H. J. Chem. Soc. (A) 1971, 2334.