Catalytic asymmetric carbon-carbon bond-forming reaction utilizing rare earth metal complexes

Pure and Applied Chemistry

Volumn 68, Issue 3, 1996, Pages 523-530

  Shibasaki, Masakatsu ^a   Sasai, Hiroaki ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000679569     PISSN: 00334545     EISSN: None     Source Type: Journal    
DOI: 10.1351/pac199668030523     Document Type: Article

References (24)

1. H. Sasai, T. Suzuki, S. Arai, T. Arai, and M. Shibasaki, J. Am. Chem. Soc., 114, 4418 (1992).
2. H. Sasai, T. Suzuki, N. Itoh, and M. Shibasaki, Tetrahedron Lett., 34, 851 (1993).
3. H. Sasai, T. Suzuki, N. Itoh, S. Arai, and M. Shibasaki, ibid., 34, 2657 (1993).
4. H. Sasai, T. Suzuki, N. Itoh, K. Tanaka, T. Date, K. Okamura, M. Shibasaki, J. Am. Chem. Soc., 115, 10372 (1993).
5. M. Shibasaki, and H. Sasai, J. Synth. Org. Chem. Jpn., 51, 972 (1993).
6. Performed by Shimadzu/Kratos KOMPACT MALDI III apparatus.
7. F. Hillenkamp, and M. Karas, Methods in ENZYMOLOGY, volume 193 ; Mass Spectrometry , J. A. McCloskey, Eds.; p. 280, Academic Press, Inc., San Diego (1990).
8. The molar ratio was 1:2:1:11, respectively. See reference 3.
9. w(F) = 0.048.
10. Purchased from Soekawa Chemical Co., Ltd., Tokyo, Japan.
11. H. Sasai, N. Itoh, T. Suzuki, and M. Shibasaki, Tetrahedron Lett., 34, 855 (1993).
12. H. Sasai, Y. M. A. Yamada, T. Suzuki, and M. Shibasaki, Tetrahedron, 50, 12313 (1994).
13. H. Sasai, W.-S. Kim, T. Suzuki, M. Mitsuda, J. Hasegawa, T. Ohashi, and M. Shibasaki, Tetrahedron Lett., 35, 6123 (1994).
14. H. Sasai, T. Arai, and M. Shibasaki, J. Am. Chem. Soc., 116, 1571 (1994).
15. 13C NMR spectrum of this catalyst was quite obscure; in general, rare earth complexes exist as oligomers.
16. For catalytic asymmetric Michael reactions, see: (a) M. Sawamura, H. Hamashima, and Y. Ito, J. Am. Chem. Soc. 114, 8295 (1992). (b) M. Yamaguchi, T. Shiraishi, and M. Hirama, Angew. Chem. Int. Ed. Engl. 32, 1176 (1993). (c) D. J. Cram, and G. D. Y. Sogah, J. Chem. Soc., Chem. Commun. 1981, 625-627. (d) M. Takasu, H. Wakabayashi, K. Furuta, and H. Yamamoto, Tetrahedron Lett. 29, 6943 (1988). (e) S. Aoki, S. Sasaki, and K. Koga, Tetrahedron Lett. 30, 7229 (1989). (f) R. Helder, and H. Wynberg, Tetrahedron Lett. 1975, 4057. (g) A. Sera, K. Takagi, H. Katayama, H. Yamada, and K. Matsumoto,. J. Org. Chem. 53, 1157 (1988). (h) T. Yura, N. Iwasawa, K. Narasaka, and T. Mukaiyama, Chem. Lett. 1988, 1025. (i) B. E. Rossiter, and N. M. Swingle, Chem. Rev. 92, 771 (1992) and references cited therein.
17. For catalytic asymmetric Michael reactions, see: (a) M. Sawamura, H. Hamashima, and Y. Ito, J. Am. Chem. Soc. 114, 8295 (1992). (b) M. Yamaguchi, T. Shiraishi, and M. Hirama, Angew. Chem. Int. Ed. Engl. 32, 1176 (1993). (c) D. J. Cram, and G. D. Y. Sogah, J. Chem. Soc., Chem. Commun. 1981, 625-627. (d) M. Takasu, H. Wakabayashi, K. Furuta, and H. Yamamoto, Tetrahedron Lett. 29, 6943 (1988). (e) S. Aoki, S. Sasaki, and K. Koga, Tetrahedron Lett. 30, 7229 (1989). (f) R. Helder, and H. Wynberg, Tetrahedron Lett. 1975, 4057. (g) A. Sera, K. Takagi, H. Katayama, H. Yamada, and K. Matsumoto,. J. Org. Chem. 53, 1157 (1988). (h) T. Yura, N. Iwasawa, K. Narasaka, and T. Mukaiyama, Chem. Lett. 1988, 1025. (i) B. E. Rossiter, and N. M. Swingle, Chem. Rev. 92, 771 (1992) and references cited therein.
18. For catalytic asymmetric Michael reactions, see: (a) M. Sawamura, H. Hamashima, and Y. Ito, J. Am. Chem. Soc. 114, 8295 (1992). (b) M. Yamaguchi, T. Shiraishi, and M. Hirama, Angew. Chem. Int. Ed. Engl. 32, 1176 (1993). (c) D. J. Cram, and G. D. Y. Sogah, J. Chem. Soc., Chem. Commun. 1981, 625-627. (d) M. Takasu, H. Wakabayashi, K. Furuta, and H. Yamamoto, Tetrahedron Lett. 29, 6943 (1988). (e) S. Aoki, S. Sasaki, and K. Koga, Tetrahedron Lett. 30, 7229 (1989). (f) R. Helder, and H. Wynberg, Tetrahedron Lett. 1975, 4057. (g) A. Sera, K. Takagi, H. Katayama, H. Yamada, and K. Matsumoto,. J. Org. Chem. 53, 1157 (1988). (h) T. Yura, N. Iwasawa, K. Narasaka, and T. Mukaiyama, Chem. Lett. 1988, 1025. (i) B. E. Rossiter, and N. M. Swingle, Chem. Rev. 92, 771 (1992) and references cited therein.
19. For catalytic asymmetric Michael reactions, see: (a) M. Sawamura, H. Hamashima, and Y. Ito, J. Am. Chem. Soc. 114, 8295 (1992). (b) M. Yamaguchi, T. Shiraishi, and M. Hirama, Angew. Chem. Int. Ed. Engl. 32, 1176 (1993). (c) D. J. Cram, and G. D. Y. Sogah, J. Chem. Soc., Chem. Commun. 1981, 625-627. (d) M. Takasu, H. Wakabayashi, K. Furuta, and H. Yamamoto, Tetrahedron Lett. 29, 6943 (1988). (e) S. Aoki, S. Sasaki, and K. Koga, Tetrahedron Lett. 30, 7229 (1989). (f) R. Helder, and H. Wynberg, Tetrahedron Lett. 1975, 4057. (g) A. Sera, K. Takagi, H. Katayama, H. Yamada, and K. Matsumoto,. J. Org. Chem. 53, 1157 (1988). (h) T. Yura, N. Iwasawa, K. Narasaka, and T. Mukaiyama, Chem. Lett. 1988, 1025. (i) B. E. Rossiter, and N. M. Swingle, Chem. Rev. 92, 771 (1992) and references cited therein.
20. For catalytic asymmetric Michael reactions, see: (a) M. Sawamura, H. Hamashima, and Y. Ito, J. Am. Chem. Soc. 114, 8295 (1992). (b) M. Yamaguchi, T. Shiraishi, and M. Hirama, Angew. Chem. Int. Ed. Engl. 32, 1176 (1993). (c) D. J. Cram, and G. D. Y. Sogah, J. Chem. Soc., Chem. Commun. 1981, 625-627. (d) M. Takasu, H. Wakabayashi, K. Furuta, and H. Yamamoto, Tetrahedron Lett. 29, 6943 (1988). (e) S. Aoki, S. Sasaki, and K. Koga, Tetrahedron Lett. 30, 7229 (1989). (f) R. Helder, and H. Wynberg, Tetrahedron Lett. 1975, 4057. (g) A. Sera, K. Takagi, H. Katayama, H. Yamada, and K. Matsumoto,. J. Org. Chem. 53, 1157 (1988). (h) T. Yura, N. Iwasawa, K. Narasaka, and T. Mukaiyama, Chem. Lett. 1988, 1025. (i) B. E. Rossiter, and N. M. Swingle, Chem. Rev. 92, 771 (1992) and references cited therein.
21. For catalytic asymmetric Michael reactions, see: (a) M. Sawamura, H. Hamashima, and Y. Ito, J. Am. Chem. Soc. 114, 8295 (1992). (b) M. Yamaguchi, T. Shiraishi, and M. Hirama, Angew. Chem. Int. Ed. Engl. 32, 1176 (1993). (c) D. J. Cram, and G. D. Y. Sogah, J. Chem. Soc., Chem. Commun. 1981, 625-627. (d) M. Takasu, H. Wakabayashi, K. Furuta, and H. Yamamoto, Tetrahedron Lett. 29, 6943 (1988). (e) S. Aoki, S. Sasaki, and K. Koga, Tetrahedron Lett. 30, 7229 (1989). (f) R. Helder, and H. Wynberg, Tetrahedron Lett. 1975, 4057. (g) A. Sera, K. Takagi, H. Katayama, H. Yamada, and K. Matsumoto,. J. Org. Chem. 53, 1157 (1988). (h) T. Yura, N. Iwasawa, K. Narasaka, and T. Mukaiyama, Chem. Lett. 1988, 1025. (i) B. E. Rossiter, and N. M. Swingle, Chem. Rev. 92, 771 (1992) and references cited therein.
22. For catalytic asymmetric Michael reactions, see: (a) M. Sawamura, H. Hamashima, and Y. Ito, J. Am. Chem. Soc. 114, 8295 (1992). (b) M. Yamaguchi, T. Shiraishi, and M. Hirama, Angew. Chem. Int. Ed. Engl. 32, 1176 (1993). (c) D. J. Cram, and G. D. Y. Sogah, J. Chem. Soc., Chem. Commun. 1981, 625-627. (d) M. Takasu, H. Wakabayashi, K. Furuta, and H. Yamamoto, Tetrahedron Lett. 29, 6943 (1988). (e) S. Aoki, S. Sasaki, and K. Koga, Tetrahedron Lett. 30, 7229 (1989). (f) R. Helder, and H. Wynberg, Tetrahedron Lett. 1975, 4057. (g) A. Sera, K. Takagi, H. Katayama, H. Yamada, and K. Matsumoto,. J. Org. Chem. 53, 1157 (1988). (h) T. Yura, N. Iwasawa, K. Narasaka, and T. Mukaiyama, Chem. Lett. 1988, 1025. (i) B. E. Rossiter, and N. M. Swingle, Chem. Rev. 92, 771 (1992) and references cited therein.
23. For catalytic asymmetric Michael reactions, see: (a) M. Sawamura, H. Hamashima, and Y. Ito, J. Am. Chem. Soc. 114, 8295 (1992). (b) M. Yamaguchi, T. Shiraishi, and M. Hirama, Angew. Chem. Int. Ed. Engl. 32, 1176 (1993). (c) D. J. Cram, and G. D. Y. Sogah, J. Chem. Soc., Chem. Commun. 1981, 625-627. (d) M. Takasu, H. Wakabayashi, K. Furuta, and H. Yamamoto, Tetrahedron Lett. 29, 6943 (1988). (e) S. Aoki, S. Sasaki, and K. Koga, Tetrahedron Lett. 30, 7229 (1989). (f) R. Helder, and H. Wynberg, Tetrahedron Lett. 1975, 4057. (g) A. Sera, K. Takagi, H. Katayama, H. Yamada, and K. Matsumoto,. J. Org. Chem. 53, 1157 (1988). (h) T. Yura, N. Iwasawa, K. Narasaka, and T. Mukaiyama, Chem. Lett. 1988, 1025. (i) B. E. Rossiter, and N. M. Swingle, Chem. Rev. 92, 771 (1992) and references cited therein.
24. For catalytic asymmetric Michael reactions, see: (a) M. Sawamura, H. Hamashima, and Y. Ito, J. Am. Chem. Soc. 114, 8295 (1992). (b) M. Yamaguchi, T. Shiraishi, and M. Hirama, Angew. Chem. Int. Ed. Engl. 32, 1176 (1993). (c) D. J. Cram, and G. D. Y. Sogah, J. Chem. Soc., Chem. Commun. 1981, 625-627. (d) M. Takasu, H. Wakabayashi, K. Furuta, and H. Yamamoto, Tetrahedron Lett. 29, 6943 (1988). (e) S. Aoki, S. Sasaki, and K. Koga, Tetrahedron Lett. 30, 7229 (1989). (f) R. Helder, and H. Wynberg, Tetrahedron Lett. 1975, 4057. (g) A. Sera, K. Takagi, H. Katayama, H. Yamada, and K. Matsumoto,. J. Org. Chem. 53, 1157 (1988). (h) T. Yura, N. Iwasawa, K. Narasaka, and T. Mukaiyama, Chem. Lett. 1988, 1025. (i) B. E. Rossiter, and N. M. Swingle, Chem. Rev. 92, 771 (1992) and references cited therein.