Catalytic asymmetric Michael reaction promoted by the La-Na-BINOL complex (LSB). Enantioface selection on Michael donors

Tetrahedron Letters

Volumn 37, Issue 31, 1996, Pages 5561-5564

  Sasai, Hiroaki ^a   Emori, Eita ^a   Arai, Takayoshi ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOALKANONE; KETONE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030605817     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01156-2     Document Type: Article

References (32)

1. 1. For previously reported catalytic asymmetric Michael reactions of Type I, see: (a) Helder, R.; Wynberg, H. Tetrahedron Lett. 1975, 4057-4060.
2. (b) Hermann, K.; Wynberg, H. J. Org, Chem. 1979, 44, 2238-2244.
3. (c) Cram, D. J.; Sogah, G. D. Y. J. Chem. Soc., Chem. Commun. 1981, 625-627. Brunner, H.; Hammer, B. Angew. Chem. Int. Ed. Engl. 1984, 23, 312-313.
4. (c) Cram, D. J.; Sogah, G. D. Y. J. Chem. Soc., Chem. Commun. 1981, 625-627. Brunner, H.; Hammer, B. Angew. Chem. Int. Ed. Engl. 1984, 23, 312-313.
5. (d) Sera, A.; Takagi, K.; Katayama, H.; Yamada, H.; Matsumoto, K. J. Org. Chem. 1988, 53, 1157-1161.
6. (e) Tamai, Y.; Kamifuku, A.; Koshiishi, E.; Miyano, S. Chem. Lett. 1995, 957-958.
7. (f) Desimoni, G.; Dusi, G.; Faita, G.; Quadrelli, P.; Righetti, P. Tetrahrdron 1995, 51, 4131-4144.
8. And see also: (g) Aoki, S.; Sasaki, S.; Koga, K. Tetrahedron Lett. 1989, 30, 7229-7230.
9. (h) Sawamura, M. Hamashima, H.; Shinoto, H.; Ito, Y. Tetrahedron Lett. 1995, 36, 6479-6482 and references cited therein.
10. 2. For previously reported catalytic asymmetric Michael reactions of Type II, see: (a) Takasu, M.; Wakabayashi, H.; Furuta, K.; Yamamoto, H. Tetrahedron Lett. 1988, 29, 6943-6946.
11. (b) Aoki, S.; Sasaki, S.; Koga, K. Heterocycles 1992, 33, 493-495.
12. (c) Yamaguchi, M.; Shiraishi, T.; Hirama, M. Angew. Chem. Int. Ed. Engl. 1993, 32, 1176-1178.
13. (d) Yamaguchi, M.; Shiraishi, T.; Igarashi Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 8233-8236.
14. (e) Kawara, A.; Taguchi, T. Tetrahedron Lett. 1994, 35, 8805-8808.
15. (f) Sasai, H.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1994, 116, 1571-1572.
16. (g) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194-6198.
17. (h) Arai, T.; Sasai, H.; Aoe, K.; Okamura, K.; Date, T.; Shibasaki, M. Angew. Chem. Int. Ed. Engl. 1996, 35, 104-106.
18. 3. For La-Li-BINOL complex (LLB), see: (a) Sasai, H.; Suzuki, T.; Arai, S.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1992, 114, 4418-4420.
19. (b) Sasai, H.; Suzuki, T.; Itoh, N.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 851-854.
20. (c) Sasai, H.; Itoh, N.; Suzuki, T.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 855-858.
21. (d) Sasai, H.; Suzuki, T.; Itoh, N.; Arai, S.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 2657-2660.
22. (e) Sasai, H.; Kim, W.-S.; Suzuki, T.; Shibasaki, M.; Mitsuda, M.; Hasegawa, J.; Ohashi, T. Tetrahedron Lett. 1994, 35, 6123-6126.
23. (f) Sasai, H.; Yamada, Y. M. A.; Suzuki, T.; Shibasaki, M. Tetrahedron 1994, 50, 12313-12318.
24. (g) Sasai, H.; Suzuki, T.; Itoh, N.; Tanaka, K.; Date, T.; Okamura, K.; Shibasaki, M. J. Am. Chem. Soc. 1993, 115, 10372-10373.
25. (h) Sasai, H.; Tokunaga, T.; Watanabe, S.; Suzuki, T.; Itoh, N.; Shibasaki M. J. Org. Chem. 1995, 60, 7388-7389.
26. For La-K-BINOL complex (LPB), see (i) Sasai, H.; Arai, S.; Tahara, Y.; Shibasaki, M. J. Org. Chem. 1995, 60, 6656-6657.
27. 4. Enantiomeric excess was determined as described in the footnote of Table 2.
28. 2O.
29. 2 (88% ee in 97% yield for 24 h at 0 °C in THF).
30. 7. The absolute configurations of the Michael adducts were determined by comparison of their optical rotation values with those reported in the literature. For 3, 7, and 15, see: Tomioka, K.; Seo, W.; Ando, K.; Koga, K. Tetrahedron Lett. 1987, 28, 6637-6640. The absolute configuration of 5 was also determined after 5 had been converted into 3. For the absolute configurations of 9 and 13, see references 2f and 1e, respectively. The absolute configurations of 11 and 18 were presumed to be the same as for 9 and 15, on the basis of their optical rotation data.
31. 2, 3 was obtained in only 5% ee.
32. +.