Asymmetric Michael addition of malonate anions to prochiral acceptors catalyzed by L-proline rubidium salt

Journal of Organic Chemistry

Volumn 61, Issue 10, 1996, Pages 3520-3530

  Yamaguchi, Masahiko ^a   Shiraishi, Tai ^a   Hirama, Masahiro ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0343967492     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960216c     Document Type: Article

References (86)

1. A review: Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon Press. Oxford. 1992.
2. For recent examples, see: Desimoni, G.; Quadrelli, P.; Righetti, P. P. Tetrahedron 1990, 46, 2927. Brunner, H.; Zintl, H. Monatsh, Chem. 1991, 122, 841. Dehmlow, E. W.; Knufinke, V. Liebigs Ann. Chem. 1992, 283.
3. For recent examples, see: Desimoni, G.; Quadrelli, P.; Righetti, P. P. Tetrahedron 1990, 46, 2927. Brunner, H.; Zintl, H. Monatsh, Chem. 1991, 122, 841. Dehmlow, E. W.; Knufinke, V. Liebigs Ann. Chem. 1992, 283.
4. For recent examples, see: Desimoni, G.; Quadrelli, P.; Righetti, P. P. Tetrahedron 1990, 46, 2927. Brunner, H.; Zintl, H. Monatsh, Chem. 1991, 122, 841. Dehmlow, E. W.; Knufinke, V. Liebigs Ann. Chem. 1992, 283.
5. Sawamura, H.; Hamashima, H.; Ito, Y. J. Am. Chem. Soc. 1992, 114, 8295;
6. Tetrahedron 1994, 50, 4439.
7. Crosby J.; Stoddart, J. F.; Sun, X.; Venner, M. R. W. Synthesis 1993, 141.
8. Bonadies, F.; Lattanzi, A.; Orelli, L. R.; Pesci, S.; Scettri, A. Tetrahedron Lett. 1993, 34, 7649.
9. Riant, O.; Kagan, H. B., Ricard, L. Tetrahedron 1994, 50, 4543.
10. Kumamoto, T.; Aoki, S.; Nakajima, M.; Koga, K. Tetrahedron: Asymmetry 1994, 5, 1431.
11. Brunet, E.; Poveda, A. M. Rabasco, D.; Oreja, E.; Font, L. M.; Batra, M. S.; Rodríguez-Ubis, J. C. Tetrahedron: Asymmetry 1994, 5, 935.
12. Töke, L.; Fenichel, L.; Albert, M. Tetrahedron Lett. 1995, 36, 5951.
13. See the following for the recent examples.; also see references cited therein: Takasu, M.; Wakabayashi, H.; Furuta, K.; Yamamoto, H. Tetrahedron Lett. 1988, 29, 6943. Sera, A.; Takagi, K.; Katayama, H.; Yamada, H.; Matsumoto, K. J. Org. Chem. 1988, 53, 1157. Iwasawa, N.; Yura, T.; Mukaiyama, T. Tetrahedron 1989, 45, 1197. Loupy, A.; Sansoulet, J.; Zaparucha, A.; Merienne, C. Tetrahedron Lett. 1989, 30, 333. Botteghi, C.; Paganelli, S.; Schionato, A.; Boga, C.; Fava, A. J. Mol. Catal. 1991, 66, 7. Hayashi, Y.; Otaka, K.; Saito, N.; Narasaka, K. Bull. Chem. Soc. Jpn. 1991, 64, 2122. Hirai, Y.; Terada, T.; Katoh, H.; Sonohara, S.; Momose, T. Heterocycles 1991, 32, 7. Aoki, S.; Sasaki, S.; Koga, K. Heterocycles 1992, 33, 493.
14. See the following for the recent examples.; also see references cited therein: Takasu, M.; Wakabayashi, H.; Furuta, K.; Yamamoto, H. Tetrahedron Lett. 1988, 29, 6943. Sera, A.; Takagi, K.; Katayama, H.; Yamada, H.; Matsumoto, K. J. Org. Chem. 1988, 53, 1157. Iwasawa, N.; Yura, T.; Mukaiyama, T. Tetrahedron 1989, 45, 1197. Loupy, A.; Sansoulet, J.; Zaparucha, A.; Merienne, C. Tetrahedron Lett. 1989, 30, 333. Botteghi, C.; Paganelli, S.; Schionato, A.; Boga, C.; Fava, A. J. Mol. Catal. 1991, 66, 7. Hayashi, Y.; Otaka, K.; Saito, N.; Narasaka, K. Bull. Chem. Soc. Jpn. 1991, 64, 2122. Hirai, Y.; Terada, T.; Katoh, H.; Sonohara, S.; Momose, T. Heterocycles 1991, 32, 7. Aoki, S.; Sasaki, S.; Koga, K. Heterocycles 1992, 33, 493.
15. See the following for the recent examples.; also see references cited therein: Takasu, M.; Wakabayashi, H.; Furuta, K.; Yamamoto, H. Tetrahedron Lett. 1988, 29, 6943. Sera, A.; Takagi, K.; Katayama, H.; Yamada, H.; Matsumoto, K. J. Org. Chem. 1988, 53, 1157. Iwasawa, N.; Yura, T.; Mukaiyama, T. Tetrahedron 1989, 45, 1197. Loupy, A.; Sansoulet, J.; Zaparucha, A.; Merienne, C. Tetrahedron Lett. 1989, 30, 333. Botteghi, C.; Paganelli, S.; Schionato, A.; Boga, C.; Fava, A. J. Mol. Catal. 1991, 66, 7. Hayashi, Y.; Otaka, K.; Saito, N.; Narasaka, K. Bull. Chem. Soc. Jpn. 1991, 64, 2122. Hirai, Y.; Terada, T.; Katoh, H.; Sonohara, S.; Momose, T. Heterocycles 1991, 32, 7. Aoki, S.; Sasaki, S.; Koga, K. Heterocycles 1992, 33, 493.
16. See the following for the recent examples.; also see references cited therein: Takasu, M.; Wakabayashi, H.; Furuta, K.; Yamamoto, H. Tetrahedron Lett. 1988, 29, 6943. Sera, A.; Takagi, K.; Katayama, H.; Yamada, H.; Matsumoto, K. J. Org. Chem. 1988, 53, 1157. Iwasawa, N.; Yura, T.; Mukaiyama, T. Tetrahedron 1989, 45, 1197. Loupy, A.; Sansoulet, J.; Zaparucha, A.; Merienne, C. Tetrahedron Lett. 1989, 30, 333. Botteghi, C.; Paganelli, S.; Schionato, A.; Boga, C.; Fava, A. J. Mol. Catal. 1991, 66, 7. Hayashi, Y.; Otaka, K.; Saito, N.; Narasaka, K. Bull. Chem. Soc. Jpn. 1991, 64, 2122. Hirai, Y.; Terada, T.; Katoh, H.; Sonohara, S.; Momose, T. Heterocycles 1991, 32, 7. Aoki, S.; Sasaki, S.; Koga, K. Heterocycles 1992, 33, 493.
17. See the following for the recent examples.; also see references cited therein: Takasu, M.; Wakabayashi, H.; Furuta, K.; Yamamoto, H. Tetrahedron Lett. 1988, 29, 6943. Sera, A.; Takagi, K.; Katayama, H.; Yamada, H.; Matsumoto, K. J. Org. Chem. 1988, 53, 1157. Iwasawa, N.; Yura, T.; Mukaiyama, T. Tetrahedron 1989, 45, 1197. Loupy, A.; Sansoulet, J.; Zaparucha, A.; Merienne, C. Tetrahedron Lett. 1989, 30, 333. Botteghi, C.; Paganelli, S.; Schionato, A.; Boga, C.; Fava, A. J. Mol. Catal. 1991, 66, 7. Hayashi, Y.; Otaka, K.; Saito, N.; Narasaka, K. Bull. Chem. Soc. Jpn. 1991, 64, 2122. Hirai, Y.; Terada, T.; Katoh, H.; Sonohara, S.; Momose, T. Heterocycles 1991, 32, 7. Aoki, S.; Sasaki, S.; Koga, K. Heterocycles 1992, 33, 493.
18. See the following for the recent examples.; also see references cited therein: Takasu, M.; Wakabayashi, H.; Furuta, K.; Yamamoto, H. Tetrahedron Lett. 1988, 29, 6943. Sera, A.; Takagi, K.; Katayama, H.; Yamada, H.; Matsumoto, K. J. Org. Chem. 1988, 53, 1157. Iwasawa, N.; Yura, T.; Mukaiyama, T. Tetrahedron 1989, 45, 1197. Loupy, A.; Sansoulet, J.; Zaparucha, A.; Merienne, C. Tetrahedron Lett. 1989, 30, 333. Botteghi, C.; Paganelli, S.; Schionato, A.; Boga, C.; Fava, A. J. Mol. Catal. 1991, 66, 7. Hayashi, Y.; Otaka, K.; Saito, N.; Narasaka, K. Bull. Chem. Soc. Jpn. 1991, 64, 2122. Hirai, Y.; Terada, T.; Katoh, H.; Sonohara, S.; Momose, T. Heterocycles 1991, 32, 7. Aoki, S.; Sasaki, S.; Koga, K. Heterocycles 1992, 33, 493.
19. See the following for the recent examples.; also see references cited therein: Takasu, M.; Wakabayashi, H.; Furuta, K.; Yamamoto, H. Tetrahedron Lett. 1988, 29, 6943. Sera, A.; Takagi, K.; Katayama, H.; Yamada, H.; Matsumoto, K. J. Org. Chem. 1988, 53, 1157. Iwasawa, N.; Yura, T.; Mukaiyama, T. Tetrahedron 1989, 45, 1197. Loupy, A.; Sansoulet, J.; Zaparucha, A.; Merienne, C. Tetrahedron Lett. 1989, 30, 333. Botteghi, C.; Paganelli, S.; Schionato, A.; Boga, C.; Fava, A. J. Mol. Catal. 1991, 66, 7. Hayashi, Y.; Otaka, K.; Saito, N.; Narasaka, K. Bull. Chem. Soc. Jpn. 1991, 64, 2122. Hirai, Y.; Terada, T.; Katoh, H.; Sonohara, S.; Momose, T. Heterocycles 1991, 32, 7. Aoki, S.; Sasaki, S.; Koga, K. Heterocycles 1992, 33, 493.
20. See the following for the recent examples.; also see references cited therein: Takasu, M.; Wakabayashi, H.; Furuta, K.; Yamamoto, H. Tetrahedron Lett. 1988, 29, 6943. Sera, A.; Takagi, K.; Katayama, H.; Yamada, H.; Matsumoto, K. J. Org. Chem. 1988, 53, 1157. Iwasawa, N.; Yura, T.; Mukaiyama, T. Tetrahedron 1989, 45, 1197. Loupy, A.; Sansoulet, J.; Zaparucha, A.; Merienne, C. Tetrahedron Lett. 1989, 30, 333. Botteghi, C.; Paganelli, S.; Schionato, A.; Boga, C.; Fava, A. J. Mol. Catal. 1991, 66, 7. Hayashi, Y.; Otaka, K.; Saito, N.; Narasaka, K. Bull. Chem. Soc. Jpn. 1991, 64, 2122. Hirai, Y.; Terada, T.; Katoh, H.; Sonohara, S.; Momose, T. Heterocycles 1991, 32, 7. Aoki, S.; Sasaki, S.; Koga, K. Heterocycles 1992, 33, 493.
21. Yamaguchi, M.; Shiraishi, T.; Hirama, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1176.
22. Sasai, H.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1994, 116, 1571. Sasai, H.; Arai, T.; Satow, Y. Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194.
23. Sasai, H.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1994, 116, 1571. Sasai, H.; Arai, T.; Satow, Y. Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194.
24. Kawara, A.; Taguchi, T. Tetrahedron Lett. 1994, 35, 8805.
25. Silyl thioketene acetals were added to cyclic (Z)-enones and chalcones. As high as 90% ee was attained in the reaction of 2-cyclopentenone Kobayashi, S.; Suda, S.; Yamada, M.; Mukaiyama, T. Chem. Lett. 1994, 97.
26. Combinatory use of amine and LiX in the Horner-Wadsworth-Emmons reaction was reported: Blanchette, M. A.; Choy, W.; Davis, J. T.; Essenfeld, A. P.; Masamune, S.; Roush, W. R.; Sakai, T. Tetrahedron Lett. 1984, 25, 2183. Rathke, M. W.; Nowak, M. J. Org. Chem. 1985, 50, 2624.
27. Combinatory use of amine and LiX in the Horner-Wadsworth-Emmons reaction was reported: Blanchette, M. A.; Choy, W.; Davis, J. T.; Essenfeld, A. P.; Masamune, S.; Roush, W. R.; Sakai, T. Tetrahedron Lett. 1984, 25, 2183. Rathke, M. W.; Nowak, M. J. Org. Chem. 1985, 50, 2624.
28. Use of proline in the asymmetric Michael addition reactions of thiolate anion: Woodward, R. B.; Logusch, E.; Nambiar, K. P.; Sakan, K.; Ward, D. E.; Au-Yeung, B.-W.; Balaram, P.; Browne, L. J.; Card, P. J.; Chen, C. H.; Chênevert, R. B.; Fliri, A.; Frobel, K.; Gais, H.-J.; Garratt, D. G.; Hayakawa, K.; Heggie, W.; Hesson, D. P.; Hoppe, D.; Hoppe, I.; Hyatt, J. A.; Ikeda, D.; Jacobi, P. A.; Kim, K. S ; Kobuke, Y.; Kojima, K.; Krowicki, K.; Lee, V. J.; Leutert, T.; Malchenko, S.; Martens, J.; Matthews, R. S.; Ong, B. S.; Press, J. B.; Rajan Babu, T. V.; Rousseau, G.; Sauter, H. M.; Suzuki, M.; Tatsuta, K.; Tolbert, L. M.; Truesdale, E. A.; Uchida, I.; Ueda, Y.; Uyehara, T.; Vasella, A. T.; Vladuchick, W. C.; Wade, P. A.; Williams, R. M.; Wong, H. N.-C. J. Am. Chem. Soc. 1981, 103, 3210. Use of proline in the intramolecular Michael addition: Kozikowski, A. P.; Mugrage, B. B. J. Org. Chem. 1989, 54, 2274.
29. Use of proline in the asymmetric Michael addition reactions of thiolate anion: Woodward, R. B.; Logusch, E.; Nambiar, K. P.; Sakan, K.; Ward, D. E.; Au-Yeung, B.-W.; Balaram, P.; Browne, L. J.; Card, P. J.; Chen, C. H.; Chênevert, R. B.; Fliri, A.; Frobel, K.; Gais, H.-J.; Garratt, D. G.; Hayakawa, K.; Heggie, W.; Hesson, D. P.; Hoppe, D.; Hoppe, I.; Hyatt, J. A.; Ikeda, D.; Jacobi, P. A.; Kim, K. S ; Kobuke, Y.; Kojima, K.; Krowicki, K.; Lee, V. J.; Leutert, T.; Malchenko, S.; Martens, J.; Matthews, R. S.; Ong, B. S.; Press, J. B.; Rajan Babu, T. V.; Rousseau, G.; Sauter, H. M.; Suzuki, M.; Tatsuta, K.; Tolbert, L. M.; Truesdale, E. A.; Uchida, I.; Ueda, Y.; Uyehara, T.; Vasella, A. T.; Vladuchick, W. C.; Wade, P. A.; Williams, R. M.; Wong, H. N.-C. J. Am. Chem. Soc. 1981, 103, 3210. Use of proline in the intramolecular Michael addition: Kozikowski, A. P.; Mugrage, B. B. J. Org. Chem. 1989, 54, 2274.
30. Yamaguchi, M.; Yokota, N.; Minami, T. J. Chem. Soc., Chem. Commun. 1991, 1088.
31. Posner, G. H.; Weitzberg, M.; Hamill, T. G.; Asirvatham, E.; Cun-Heng, H.; Clardy, J. Tetrahedron 1986, 42, 2919.
32. Reetz, M. T.; Hütte, S.; Goddard, R. J. Am. Chem. Soc. 1993, 115, 9339.
33. See for example: Inoue, Y.; Yamasaki, N., Yokoyama, T.; Tai, A. J. Org. Chem. 1992, 57, 1332. Hatanaka, Y.; Hiyama, T. J. Am. Chem. Soc. 1990, 112, 7793.
34. See for example: Inoue, Y.; Yamasaki, N., Yokoyama, T.; Tai, A. J. Org. Chem. 1992, 57, 1332. Hatanaka, Y.; Hiyama, T. J. Am. Chem. Soc. 1990, 112, 7793.
35. Jackman, L. M.; Lange, B. C. Tetrahedron 1977, 35, 2737. Barlow, G. H.; Zaugg, H. E. J. Org. Chem. 1972, 37, 2246. Zaugg, H. E.; Ratajczyk, J. F.; Leonard, J. E.; Schaefer, A. D. J. Org. Chem. 1972, 37, 2249.
36. Jackman, L. M.; Lange, B. C. Tetrahedron 1977, 35, 2737. Barlow, G. H.; Zaugg, H. E. J. Org. Chem. 1972, 37, 2246. Zaugg, H. E.; Ratajczyk, J. F.; Leonard, J. E.; Schaefer, A. D. J. Org. Chem. 1972, 37, 2249.
37. Jackman, L. M.; Lange, B. C. Tetrahedron 1977, 35, 2737. Barlow, G. H.; Zaugg, H. E. J. Org. Chem. 1972, 37, 2246. Zaugg, H. E.; Ratajczyk, J. F.; Leonard, J. E.; Schaefer, A. D. J. Org. Chem. 1972, 37, 2249.
38. Hinton, J. F.; Amis, E. S. Chem. Rev. 1971, 71, 627.
39. For examples: Bhattacharyya, D. N.; Lee, C. L.; Smid, J.; Szwaec, M. J. Phys. Chem. 1956, 69, 608. Krumgalz, J. Chem. Soc., Faraday Trans. 1 1980, 76, 1887; 1982, 78, 437.
40. For examples: Bhattacharyya, D. N.; Lee, C. L.; Smid, J.; Szwaec, M. J. Phys. Chem. 1956, 69, 608. Krumgalz, J. Chem. Soc., Faraday Trans. 1 1980, 76, 1887; 1982, 78, 437.
41. For examples: Bhattacharyya, D. N.; Lee, C. L.; Smid, J.; Szwaec, M. J. Phys. Chem. 1956, 69, 608. Krumgalz, J. Chem. Soc., Faraday Trans. 1 1980, 76, 1887; 1982, 78, 437.
42. Enders, D.; Papadopoulos, K. Tetrahedron Lett. 1983, 24, 4967.
43. Tomioka, K.; Yasuda, K.; Koga, K, Tetrahedron Lett. 1986, 27, 4611.
44. de Boer, T. J.; Backer, H. J. Organic Syntheses; Wiley: New York, 1963; Collect. Vol. 4, p 225.
45. Amine-catalyzed isomerization of (Z)-unsaturated carbonyl compounds is known. See for example: Southwick, P. L.; Shozda, R. J. J. Am. Chem. Soc. 1959, 81, 3298. Rappoport, Z.; Degani, C.; Patai, S. J. Chem. Soc. 1963, 4513.
46. Amine-catalyzed isomerization of (Z)-unsaturated carbonyl compounds is known. See for example: Southwick, P. L.; Shozda, R. J. J. Am. Chem. Soc. 1959, 81, 3298. Rappoport, Z.; Degani, C.; Patai, S. J. Chem. Soc. 1963, 4513.
47. Yamamoto, K.; Iijima, M.; Ogimura, Y. Tetrahedron Lett. 1982, 23, 3711.
48. 2: Suemune, H.; Oda, K.; Sakai, K. Tetrahedron Lett. 1987, 28, 3373.
49. Yamaguchi, M.; Shiraishi, T.; Igarashi, Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 8233.
50. Tanaka, K.; Ushio, H.; Kawabata, Y.; Suzuki, H. J. Chem. Soc., Perkin Trans. 1 1991, 1445.
51. Branca, Q.; Fischli, A. Helv. Chim. Acta 1977, 60, 925.
52. Barton, D. H. R.; Crich, D.; Motherwell, W. B. Tetrahedron 1985, 41, 3901.
53. Some conjugate addition reactions rigorously require s-cis configuration of acceptors and are not applicable to cyclic enones. Hooz, J.; Layton, R. B. J. Am. Chem Soc. 1971, 93, 7320 Sinclair, J. A.; Molander, G. A.; Brown, H. C J. Am. Chem. Soc. 1977, 99, 954.
54. Some conjugate addition reactions rigorously require s-cis configuration of acceptors and are not applicable to cyclic enones. Hooz, J.; Layton, R. B. J. Am. Chem Soc. 1971, 93, 7320 Sinclair, J. A.; Molander, G. A.; Brown, H. C J. Am. Chem. Soc. 1977, 99, 954.
55. Oppolzer, W.; Loher, H. J. Helv. Chim. Acta, 1981, 64, 2808; Oppolzer, W.; Poli, G. Tetrahedron Lett. 1986, 27, 4717. For other example: Takaki, K.; Maeda, T.; Ishikawa, M. J. Org. Chem. 1989, 54, 58. Pyne, S. G., Griffith, R.; Edwards, M. Tetrahedron Lett. 1988, 29, 2089. Corey, E. J.; Hannon, F. J.; Boaz, N. W. Tetrahedron 1989, 45, 545.
56. Oppolzer, W.; Loher, H. J. Helv. Chim. Acta, 1981, 64, 2808; Oppolzer, W.; Poli, G. Tetrahedron Lett. 1986, 27, 4717. For other example: Takaki, K.; Maeda, T.; Ishikawa, M. J. Org. Chem. 1989, 54, 58. Pyne, S. G., Griffith, R.; Edwards, M. Tetrahedron Lett. 1988, 29, 2089. Corey, E. J.; Hannon, F. J.; Boaz, N. W. Tetrahedron 1989, 45, 545.
57. Oppolzer, W.; Loher, H. J. Helv. Chim. Acta, 1981, 64, 2808; Oppolzer, W.; Poli, G. Tetrahedron Lett. 1986, 27, 4717. For other example: Takaki, K.; Maeda, T.; Ishikawa, M. J. Org. Chem. 1989, 54, 58. Pyne, S. G., Griffith, R.; Edwards, M. Tetrahedron Lett. 1988, 29, 2089. Corey, E. J.; Hannon, F. J.; Boaz, N. W. Tetrahedron 1989, 45, 545.
58. Oppolzer, W.; Loher, H. J. Helv. Chim. Acta, 1981, 64, 2808; Oppolzer, W.; Poli, G. Tetrahedron Lett. 1986, 27, 4717. For other example: Takaki, K.; Maeda, T.; Ishikawa, M. J. Org. Chem. 1989, 54, 58. Pyne, S. G., Griffith, R.; Edwards, M. Tetrahedron Lett. 1988, 29, 2089. Corey, E. J.; Hannon, F. J.; Boaz, N. W. Tetrahedron 1989, 45, 545.
59. Oppolzer, W.; Loher, H. J. Helv. Chim. Acta, 1981, 64, 2808; Oppolzer, W.; Poli, G. Tetrahedron Lett. 1986, 27, 4717. For other example: Takaki, K.; Maeda, T.; Ishikawa, M. J. Org. Chem. 1989, 54, 58. Pyne, S. G., Griffith, R.; Edwards, M. Tetrahedron Lett. 1988, 29, 2089. Corey, E. J.; Hannon, F. J.; Boaz, N. W. Tetrahedron 1989, 45, 545.
60. Such stereochemical outcome was also found in addition reactions of chiral cuprate reagents: Leyendecker, F.; Jesser, F.; Ruhland, B. Tetrahedron Lett. 1981, 3601. Andersson, S.; Jagner, S.; Nilsson, M.; Urso, F. J. Organomet. Chem. 1986, 301, 257. Dieter, R. K.; Tokles, M. J. Am. Chem. Soc. 1987, 109, 2040.
61. Such stereochemical outcome was also found in addition reactions of chiral cuprate reagents: Leyendecker, F.; Jesser, F.; Ruhland, B. Tetrahedron Lett. 1981, 3601. Andersson, S.; Jagner, S.; Nilsson, M.; Urso, F. J. Organomet. Chem. 1986, 301, 257. Dieter, R. K.; Tokles, M. J. Am. Chem. Soc. 1987, 109, 2040.
62. Such stereochemical outcome was also found in addition reactions of chiral cuprate reagents: Leyendecker, F.; Jesser, F.; Ruhland, B. Tetrahedron Lett. 1981, 3601. Andersson, S.; Jagner, S.; Nilsson, M.; Urso, F. J. Organomet. Chem. 1986, 301, 257. Dieter, R. K.; Tokles, M. J. Am. Chem. Soc. 1987, 109, 2040.
63. 5 Discussion, however, is not simple here, since chalcones are unusual substrates in the asymmetric Michael addition as shown by many examples.
64. Kretchmer, R. A. J. Org. Chem. 1972, 37, 2744.
65. Importance of π-π attractive interaction between the catalyst and chalcone was indicated in the Michael addition reaction: Loupy, A.; Zaparucha, A. Tetrahedron Lett. 1993, 34, 473.
66. Example of iminium salt used in the asymmetric synthresis: Takano, S.; Iwata, H.; Ogasawara, K. Heterocycles 1978, 9, 845.
67. Sheves, M.; Nakanishi, K. J. Am. Chem. Soc. 1983, 105, 4033.
68. Conjugate addition reactions to unsaturated iminium salts: Pandit, U. K.; Cabré, F. R. M.; Gase, R. A.; de Nie-Sarink, M. J. J. Chem. Soc., Chem. Commun. 1974, 627. de Nie-Sarink, M. J.; Pandit, U. K Tetrahedron Lett. 1979, 2449.
69. Conjugate addition reactions to unsaturated iminium salts: Pandit, U. K.; Cabré, F. R. M.; Gase, R. A.; de Nie-Sarink, M. J. J. Chem. Soc., Chem. Commun. 1974, 627. de Nie-Sarink, M. J.; Pandit, U. K Tetrahedron Lett. 1979, 2449.
70. Compare: Leonard, N. J.; Paukstelis, J. V. J. Org. Chem. 1963, 28, 3021.
71. Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem. 1971, 83, 492. Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615
72. Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem. 1971, 83, 492. Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615
73. Agami, C. Bull. Soc. Chim. Fr. 1988, 499.
74. Puchot, C.; Samuel, O.; Duñach, E.; Zhao, S.; Agami, C.; Kagan, H. B. J. Am. Chem. Soc 1986, 108, 2353. Guillaneux, D.; Zhao, S.-H.; Samuel, O.; Rainford, D ; Kagan, H. B. J. Am. Chem. Soc. 1994, 116, 9430 and references therein.
75. Puchot, C.; Samuel, O.; Duñach, E.; Zhao, S.; Agami, C.; Kagan, H. B. J. Am. Chem. Soc 1986, 108, 2353. Guillaneux, D.; Zhao, S.-H.; Samuel, O.; Rainford, D ; Kagan, H. B. J. Am. Chem. Soc. 1994, 116, 9430 and references therein.
76. Goldstein, S. W., Overman, L. E.; Rabinowitz, M. H. J. Org. Chem. 1992, 57, 1179.
77. Seebach, D.; Boes, M.; Naef, R.; Schweizer, W. B. J. Am. Chem. Soc. 1983, 105, 5390.
78. Quitt, P.; Hellerbach, J.; Vogler, K. Helv. Chim. Acta 1963, 46, 327.
79. Cassal, J.-M.; Fürst, A.; Meier, W. Helv. Chim. Acta 1976, 59, 1917.
80. Howard-Lock, H. E.; Lock, C. J. L.; Martins, M. L.; Smalley, P. S.; Bell, R. A. Can. J. Chem. 1986, 64, 1215. Nagasawa, H. T.; Goon, D. J. W.; Muldoon, W. P.; Zera, R T. J. Med. Chem. 1984, 27, 591.
81. Howard-Lock, H. E.; Lock, C. J. L.; Martins, M. L.; Smalley, P. S.; Bell, R. A. Can. J. Chem. 1986, 64, 1215. Nagasawa, H. T.; Goon, D. J. W.; Muldoon, W. P.; Zera, R T. J. Med. Chem. 1984, 27, 591.
82. Cope, A. C.; Ciganek, E.; Fleckenstein, L. J.; Meisinger, M. A. P. J. Am. Chem. Soc. 1960, 82, 4651. Lillis, V.; Mckenna, J.; Mckenna, J. M.; Smith, M. J.; Taylor, P. S.; Williams, I. H. J. Chem. Soc., Perkin Trans. 2 1980, 83.
83. Cope, A. C.; Ciganek, E.; Fleckenstein, L. J.; Meisinger, M. A. P. J. Am. Chem. Soc. 1960, 82, 4651. Lillis, V.; Mckenna, J.; Mckenna, J. M.; Smith, M. J.; Taylor, P. S.; Williams, I. H. J. Chem. Soc., Perkin Trans. 2 1980, 83.
84. Cundiff, R. H.; Markunas, P. C Anal. Chem. 1956, 28, 792. Cluett, M. L. Anal. Chem. 1959, 31, 610.
85. Cundiff, R. H.; Markunas, P. C Anal. Chem. 1956, 28, 792. Cluett, M. L. Anal. Chem. 1959, 31, 610.
86. Minami, I.; Takahashi, K.; Shimizu, I.; Kimura, T.; Tsuji, J. Tetrahedron 1986, 42, 2971.