Asymmetric synthesis using palladium catalysts

Pure and Applied Chemistry

Volumn 70, Issue 2, 1998, Pages 411-414

  Sodeoka, Mikiko ^a   Shibasaki, Masakatsu ^b  

^a SAGAMI CHEMICAL RESEARCH CENTER   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002867663     PISSN: 00334545     EISSN: None     Source Type: Journal    
DOI: 10.1351/pac199870020411     Document Type: Article

References (28)

1. Y. Sato, M. Sodeoka and M. Shibasaki, J. Org. Chem. 54, 4738 (1989). M. Shibasaki and M. Sodeoka. J. Synth. Org. Chem., Japan, Engl. 52, 956 (1994), and references cited therein and also in reference 2.
2. Y. Sato, M. Sodeoka and M. Shibasaki, J. Org. Chem. 54, 4738 (1989). M. Shibasaki and M. Sodeoka. J. Synth. Org. Chem., Japan, Engl. 52, 956 (1994), and references cited therein and also in reference 2.
3. T. Ohshima, K. Kagechika, M. Adachi, M. Sodeoka and M. Shibasaki. J. Am. Chem. Soc. 118, 7108 (1996).
4. A. Kojima, T. Takemoto, M. Sodeoka and M. Shibasaki. J. Org. Chem. 61, 4876 (1996).
5. M. Sodeoka, K. Ohrai and M. Shibasaki. J. Org. Chem. 60, 2648 (1995).
6. Rh catalysts: (a) S. Sato, I. Matsuda and Y. Izumi. Tetrahedron Lett. 27, 5517 (1986). (b) S. Sato, I. Matsuda and Y. Izumi. J. Organomet. Chem. 352, 223 (1988). (c) O. A. Slough, R. G. Bergman and C. H. Heathcock. J. Am. Chem. Soc. 111, 938 (1989). (d) T. Soga, H. Takenoshita, M. Yamada and T. Mukaiyama. Bull. Chem. Soc. Jpn. 63, 3122 (1990). Pd catalysts: (e) J. Nokami, T. Mandai, H. Watanabe, H. Ohyama and J. Tsuji. J. Am. Chem. Soc. 111, 4126 (1989). Ru catalysts: (f) T. Naota, H. Taki, M. Mizuno and S.-I. Murahashi. J. Am. Chem. Soc. 111, 5954 (1989), and references cited therein.
7. Rh catalysts: (a) S. Sato, I. Matsuda and Y. Izumi. Tetrahedron Lett. 27, 5517 (1986). (b) S. Sato, I. Matsuda and Y. Izumi. J. Organomet. Chem. 352, 223 (1988). (c) O. A. Slough, R. G. Bergman and C. H. Heathcock. J. Am. Chem. Soc. 111, 938 (1989). (d) T. Soga, H. Takenoshita, M. Yamada and T. Mukaiyama. Bull. Chem. Soc. Jpn. 63, 3122 (1990). Pd catalysts: (e) J. Nokami, T. Mandai, H. Watanabe, H. Ohyama and J. Tsuji. J. Am. Chem. Soc. 111, 4126 (1989). Ru catalysts: (f) T. Naota, H. Taki, M. Mizuno and S.-I. Murahashi. J. Am. Chem. Soc. 111, 5954 (1989), and references cited therein.
8. Rh catalysts: (a) S. Sato, I. Matsuda and Y. Izumi. Tetrahedron Lett. 27, 5517 (1986). (b) S. Sato, I. Matsuda and Y. Izumi. J. Organomet. Chem. 352, 223 (1988). (c) O. A. Slough, R. G. Bergman and C. H. Heathcock. J. Am. Chem. Soc. 111, 938 (1989). (d) T. Soga, H. Takenoshita, M. Yamada and T. Mukaiyama. Bull. Chem. Soc. Jpn. 63, 3122 (1990). Pd catalysts: (e) J. Nokami, T. Mandai, H. Watanabe, H. Ohyama and J. Tsuji. J. Am. Chem. Soc. 111, 4126 (1989). Ru catalysts: (f) T. Naota, H. Taki, M. Mizuno and S.-I. Murahashi. J. Am. Chem. Soc. 111, 5954 (1989), and references cited therein.
9. Rh catalysts: (a) S. Sato, I. Matsuda and Y. Izumi. Tetrahedron Lett. 27, 5517 (1986). (b) S. Sato, I. Matsuda and Y. Izumi. J. Organomet. Chem. 352, 223 (1988). (c) O. A. Slough, R. G. Bergman and C. H. Heathcock. J. Am. Chem. Soc. 111, 938 (1989). (d) T. Soga, H. Takenoshita, M. Yamada and T. Mukaiyama. Bull. Chem. Soc. Jpn. 63, 3122 (1990). Pd catalysts: (e) J. Nokami, T. Mandai, H. Watanabe, H. Ohyama and J. Tsuji. J. Am. Chem. Soc. 111, 4126 (1989). Ru catalysts: (f) T. Naota, H. Taki, M. Mizuno and S.-I. Murahashi. J. Am. Chem. Soc. 111, 5954 (1989), and references cited therein.
10. Rh catalysts: (a) S. Sato, I. Matsuda and Y. Izumi. Tetrahedron Lett. 27, 5517 (1986). (b) S. Sato, I. Matsuda and Y. Izumi. J. Organomet. Chem. 352, 223 (1988). (c) O. A. Slough, R. G. Bergman and C. H. Heathcock. J. Am. Chem. Soc. 111, 938 (1989). (d) T. Soga, H. Takenoshita, M. Yamada and T. Mukaiyama. Bull. Chem. Soc. Jpn. 63, 3122 (1990). Pd catalysts: (e) J. Nokami, T. Mandai, H. Watanabe, H. Ohyama and J. Tsuji. J. Am. Chem. Soc. 111, 4126 (1989). Ru catalysts: (f) T. Naota, H. Taki, M. Mizuno and S.-I. Murahashi. J. Am. Chem. Soc. 111, 5954 (1989), and references cited therein.
11. Rh catalysts: (a) S. Sato, I. Matsuda and Y. Izumi. Tetrahedron Lett. 27, 5517 (1986). (b) S. Sato, I. Matsuda and Y. Izumi. J. Organomet. Chem. 352, 223 (1988). (c) O. A. Slough, R. G. Bergman and C. H. Heathcock. J. Am. Chem. Soc. 111, 938 (1989). (d) T. Soga, H. Takenoshita, M. Yamada and T. Mukaiyama. Bull. Chem. Soc. Jpn. 63, 3122 (1990). Pd catalysts: (e) J. Nokami, T. Mandai, H. Watanabe, H. Ohyama and J. Tsuji. J. Am. Chem. Soc. 111, 4126 (1989). Ru catalysts: (f) T. Naota, H. Taki, M. Mizuno and S.-I. Murahashi. J. Am. Chem. Soc. 111, 5954 (1989), and references cited therein.
12. Au(I) and Ag(I) complexes have been reported to catalyze the asymmetric aldol-type reaction of isonitriles with aldehydes. See: (a) Y. Ito, M. Sawamura and T. Hayashi. J. Am. Chem. Soc. 108, 6405 (1986). (b) T. Hayashi, M. Sawamura and Y. Ito. Tetrahedron Lett. 48, 1999 (1992), and references cited therein. Recently the Pd(II) complex-catalyzed reaction of isonitriles has also been reported (maximum 14% ee), see: (c) R. Nesper, P. S. Pregosin, K. Püntener, M. Wörle. Helv. Chim. Acta 76, 2239 (1993).
13. Au(I) and Ag(I) complexes have been reported to catalyze the asymmetric aldol-type reaction of isonitriles with aldehydes. See: (a) Y. Ito, M. Sawamura and T. Hayashi. J. Am. Chem. Soc. 108, 6405 (1986). (b) T. Hayashi, M. Sawamura and Y. Ito. Tetrahedron Lett. 48, 1999 (1992), and references cited therein. Recently the Pd(II) complex-catalyzed reaction of isonitriles has also been reported (maximum 14% ee), see: (c) R. Nesper, P. S. Pregosin, K. Püntener, M. Wörle. Helv. Chim. Acta 76, 2239 (1993).
14. Au(I) and Ag(I) complexes have been reported to catalyze the asymmetric aldol-type reaction of isonitriles with aldehydes. See: (a) Y. Ito, M. Sawamura and T. Hayashi. J. Am. Chem. Soc. 108, 6405 (1986). (b) T. Hayashi, M. Sawamura and Y. Ito. Tetrahedron Lett. 48, 1999 (1992), and references cited therein. Recently the Pd(II) complex-catalyzed reaction of isonitriles has also been reported (maximum 14% ee), see: (c) R. Nesper, P. S. Pregosin, K. Püntener, M. Wörle. Helv. Chim. Acta 76, 2239 (1993).
15. (a) M. T. Reetz and A. E. Vougioukas. Tetrahedron Lett. 28, 793 (1987) (maximum 12% ee).
16. (b) G. H. P. Roos, R. J. Haines and C. E. Raab. Synth. Commun. 23, 1251 (1993) (maximum 23% ee).
17. F. Ozawa, A. Kubo, Y. Matsumoto, T. Hayashi, E. Nishioka, K. Yanagi and K. Moriguchi. Organometallics 12, 4188 (1993).
18. (a) E. J. Moore, D. A. Straus, J. Armantrout, B. D. Santarsiero, R. H. Grubbs and J. E. Bercaw. J. Am. Chem. Soc. 105, 2168 (1983) (Zr).
19. (b) J. R. Stille and R. H. Grubbs. J. Am. Chem. Soc. 105, 1664 (1983) (Ti).
20. 8 Since these two complexes were found to show basically the same reactivity and asymmetric induction, we used both complexes for this research.
21. M. Sodeoka, R. Tokunoh and M. Shibasaki, unpublished results.
22. 2 (5 mol %) and (R)-Tol-BINAP (5 mol %) in wet DMF in the presence of 4A molecular sieves also effectively catalyzed the condensation of 1 with 2 to give 4 (98%, 69% ee) and 5 (2%, 64% ee).
23. M. Sodeoka, E. Hagiwara, K. Ohrai and M. Shibasaki, unpublished results.
24. 2O: 4%, 67% ee).
25. Y. Ito, T. Hirao, A. Mochizuki and T. Saegusa. J. Org. Chem. 43, 1011 (1978).
26. M. Sodeoka and E. Hagiwara, unpublished results.
27. Reaction concentration was important for the reactivity and asymmetric induction when TMU was used as the solvent. Reaction at ca. 0.67 M of 2 in TMU was slower than that at 0.1 M, and the optical yield of the product decreased from 84% ee to 76% ee. No dependence of optical yield on concentration was observed for the reaction in DMF.
28. iPrOH, 9:1).