Enantioselective conjugate additions of organolithiums to BHA enoates mediated by a chiral ligand

Tetrahedron Letters

Volumn 38, Issue 52, 1997, Pages 8973-8976

  Asano, Yasutomi ^a   Iida, Akira ^a   Tomioka, Kiyoshi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

HEXANE; LIGAND; LITHIUM; ORGANOLITHIUM COMPOUND; TOLUENE;

ARTICLE; CHIRALITY; CONJUGATE; CONTROLLED STUDY; DRUG SYNTHESIS; ENANTIOMER; STEREOCHEMISTRY;

EID: 0030823091     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10366-5     Document Type: Article

References (38)

1. Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis, Tetrahedron Organic Chemistry Series Vol. 9, 1992, Pergamon Press, Oxford.
2. Review for asymmetric conjugate addition reaction: Tomioka, K.; Koga, K. in Asymmetric Synthesis Vol. 2, Academic Press, New York, 1983, chapter 7; Posner, G. H. ibid, chapter 8; Lutomoski, K. A.; Meyers, A. I. in Asymmetric Synthesis Vol. 3, Academic Press, New York, 1984, chapter 3; Oppolzer, W. Tetrahedron 1987,43, 1969-2004. Recent report: Oppolzer, W.; Poli, G.; Kingma, A. J.; Starkemann, C.; Bernardinelli, G. Helv. Chim. Acta 1987, 70, 2201-2214; Rück, K.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 694-696; Fang, C.-L.; Ogawa, T.; Suemune, H.; Sakai, K. Tetrahedron Asymm. 1991, 2, 389-398; Stephan, E.; Rocher, R.; Aubouet, J.; Pourcelot, G.; Cresson, P. Tetrahedron Asymm. 1993, 5, 41-44; Wu. M.-J.; Yeh, J.-Y. Tetrahedron 1994, 50, 1073-1082; Tsuge, H.; Takumi, K.; Nagai, T.; Okano, T.; Eguchi, S.; Kimoto, H. Tetrahedron 1997, 53, 823-838.
3. Review for asymmetric conjugate addition reaction: Tomioka, K.; Koga, K. in Asymmetric Synthesis Vol. 2, Academic Press, New York, 1983, chapter 7; Posner, G. H. ibid, chapter 8; Lutomoski, K. A.; Meyers, A. I. in Asymmetric Synthesis Vol. 3, Academic Press, New York, 1984, chapter 3; Oppolzer, W. Tetrahedron 1987,43, 1969-2004. Recent report: Oppolzer, W.; Poli, G.; Kingma, A. J.; Starkemann, C.; Bernardinelli, G. Helv. Chim. Acta 1987, 70, 2201-2214; Rück, K.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 694-696; Fang, C.-L.; Ogawa, T.; Suemune, H.; Sakai, K. Tetrahedron Asymm. 1991, 2, 389-398; Stephan, E.; Rocher, R.; Aubouet, J.; Pourcelot, G.; Cresson, P. Tetrahedron Asymm. 1993, 5, 41-44; Wu. M.-J.; Yeh, J.-Y. Tetrahedron 1994, 50, 1073-1082; Tsuge, H.; Takumi, K.; Nagai, T.; Okano, T.; Eguchi, S.; Kimoto, H. Tetrahedron 1997, 53, 823-838.
4. Review for asymmetric conjugate addition reaction: Tomioka, K.; Koga, K. in Asymmetric Synthesis Vol. 2, Academic Press, New York, 1983, chapter 7; Posner, G. H. ibid, chapter 8; Lutomoski, K. A.; Meyers, A. I. in Asymmetric Synthesis Vol. 3, Academic Press, New York, 1984, chapter 3; Oppolzer, W. Tetrahedron 1987,43, 1969-2004. Recent report: Oppolzer, W.; Poli, G.; Kingma, A. J.; Starkemann, C.; Bernardinelli, G. Helv. Chim. Acta 1987, 70, 2201-2214; Rück, K.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 694-696; Fang, C.-L.; Ogawa, T.; Suemune, H.; Sakai, K. Tetrahedron Asymm. 1991, 2, 389-398; Stephan, E.; Rocher, R.; Aubouet, J.; Pourcelot, G.; Cresson, P. Tetrahedron Asymm. 1993, 5, 41-44; Wu. M.-J.; Yeh, J.-Y. Tetrahedron 1994, 50, 1073-1082; Tsuge, H.; Takumi, K.; Nagai, T.; Okano, T.; Eguchi, S.; Kimoto, H. Tetrahedron 1997, 53, 823-838.
5. Review for asymmetric conjugate addition reaction: Tomioka, K.; Koga, K. in Asymmetric Synthesis Vol. 2, Academic Press, New York, 1983, chapter 7; Posner, G. H. ibid, chapter 8; Lutomoski, K. A.; Meyers, A. I. in Asymmetric Synthesis Vol. 3, Academic Press, New York, 1984, chapter 3; Oppolzer, W. Tetrahedron 1987,43, 1969-2004. Recent report: Oppolzer, W.; Poli, G.; Kingma, A. J.; Starkemann, C.; Bernardinelli, G. Helv. Chim. Acta 1987, 70, 2201-2214; Rück, K.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 694-696; Fang, C.-L.; Ogawa, T.; Suemune, H.; Sakai, K. Tetrahedron Asymm. 1991, 2, 389-398; Stephan, E.; Rocher, R.; Aubouet, J.; Pourcelot, G.; Cresson, P. Tetrahedron Asymm. 1993, 5, 41-44; Wu. M.-J.; Yeh, J.-Y. Tetrahedron 1994, 50, 1073-1082; Tsuge, H.; Takumi, K.; Nagai, T.; Okano, T.; Eguchi, S.; Kimoto, H. Tetrahedron 1997, 53, 823-838.
6. Review for asymmetric conjugate addition reaction: Tomioka, K.; Koga, K. in Asymmetric Synthesis Vol. 2, Academic Press, New York, 1983, chapter 7; Posner, G. H. ibid, chapter 8; Lutomoski, K. A.; Meyers, A. I. in Asymmetric Synthesis Vol. 3, Academic Press, New York, 1984, chapter 3; Oppolzer, W. Tetrahedron 1987,43, 1969-2004. Recent report: Oppolzer, W.; Poli, G.; Kingma, A. J.; Starkemann, C.; Bernardinelli, G. Helv. Chim. Acta 1987, 70, 2201-2214; Rück, K.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 694-696; Fang, C.-L.; Ogawa, T.; Suemune, H.; Sakai, K. Tetrahedron Asymm. 1991, 2, 389-398; Stephan, E.; Rocher, R.; Aubouet, J.; Pourcelot, G.; Cresson, P. Tetrahedron Asymm. 1993, 5, 41-44; Wu. M.-J.; Yeh, J.-Y. Tetrahedron 1994, 50, 1073-1082; Tsuge, H.; Takumi, K.; Nagai, T.; Okano, T.; Eguchi, S.; Kimoto, H. Tetrahedron 1997, 53, 823-838.
7. Review for asymmetric conjugate addition reaction: Tomioka, K.; Koga, K. in Asymmetric Synthesis Vol. 2, Academic Press, New York, 1983, chapter 7; Posner, G. H. ibid, chapter 8; Lutomoski, K. A.; Meyers, A. I. in Asymmetric Synthesis Vol. 3, Academic Press, New York, 1984, chapter 3; Oppolzer, W. Tetrahedron 1987,43, 1969-2004. Recent report: Oppolzer, W.; Poli, G.; Kingma, A. J.; Starkemann, C.; Bernardinelli, G. Helv. Chim. Acta 1987, 70, 2201-2214; Rück, K.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 694-696; Fang, C.-L.; Ogawa, T.; Suemune, H.; Sakai, K. Tetrahedron Asymm. 1991, 2, 389-398; Stephan, E.; Rocher, R.; Aubouet, J.; Pourcelot, G.; Cresson, P. Tetrahedron Asymm. 1993, 5, 41-44; Wu. M.-J.; Yeh, J.-Y. Tetrahedron 1994, 50, 1073-1082; Tsuge, H.; Takumi, K.; Nagai, T.; Okano, T.; Eguchi, S.; Kimoto, H. Tetrahedron 1997, 53, 823-838.
8. Review for asymmetric conjugate addition reaction: Tomioka, K.; Koga, K. in Asymmetric Synthesis Vol. 2, Academic Press, New York, 1983, chapter 7; Posner, G. H. ibid, chapter 8; Lutomoski, K. A.; Meyers, A. I. in Asymmetric Synthesis Vol. 3, Academic Press, New York, 1984, chapter 3; Oppolzer, W. Tetrahedron 1987,43, 1969-2004. Recent report: Oppolzer, W.; Poli, G.; Kingma, A. J.; Starkemann, C.; Bernardinelli, G. Helv. Chim. Acta 1987, 70, 2201-2214; Rück, K.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 694-696; Fang, C.-L.; Ogawa, T.; Suemune, H.; Sakai, K. Tetrahedron Asymm. 1991, 2, 389-398; Stephan, E.; Rocher, R.; Aubouet, J.; Pourcelot, G.; Cresson, P. Tetrahedron Asymm. 1993, 5, 41-44; Wu. M.-J.; Yeh, J.-Y. Tetrahedron 1994, 50, 1073-1082; Tsuge, H.; Takumi, K.; Nagai, T.; Okano, T.; Eguchi, S.; Kimoto, H. Tetrahedron 1997, 53, 823-838.
9. Review for asymmetric conjugate addition reaction: Tomioka, K.; Koga, K. in Asymmetric Synthesis Vol. 2, Academic Press, New York, 1983, chapter 7; Posner, G. H. ibid, chapter 8; Lutomoski, K. A.; Meyers, A. I. in Asymmetric Synthesis Vol. 3, Academic Press, New York, 1984, chapter 3; Oppolzer, W. Tetrahedron 1987,43, 1969-2004. Recent report: Oppolzer, W.; Poli, G.; Kingma, A. J.; Starkemann, C.; Bernardinelli, G. Helv. Chim. Acta 1987, 70, 2201-2214; Rück, K.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 694-696; Fang, C.-L.; Ogawa, T.; Suemune, H.; Sakai, K. Tetrahedron Asymm. 1991, 2, 389-398; Stephan, E.; Rocher, R.; Aubouet, J.; Pourcelot, G.; Cresson, P. Tetrahedron Asymm. 1993, 5, 41-44; Wu. M.-J.; Yeh, J.-Y. Tetrahedron 1994, 50, 1073-1082; Tsuge, H.; Takumi, K.; Nagai, T.; Okano, T.; Eguchi, S.; Kimoto, H. Tetrahedron 1997, 53, 823-838.
10. Review for asymmetric conjugate addition reaction: Tomioka, K.; Koga, K. in Asymmetric Synthesis Vol. 2, Academic Press, New York, 1983, chapter 7; Posner, G. H. ibid, chapter 8; Lutomoski, K. A.; Meyers, A. I. in Asymmetric Synthesis Vol. 3, Academic Press, New York, 1984, chapter 3; Oppolzer, W. Tetrahedron 1987,43, 1969-2004. Recent report: Oppolzer, W.; Poli, G.; Kingma, A. J.; Starkemann, C.; Bernardinelli, G. Helv. Chim. Acta 1987, 70, 2201-2214; Rück, K.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 694-696; Fang, C.-L.; Ogawa, T.; Suemune, H.; Sakai, K. Tetrahedron Asymm. 1991, 2, 389-398; Stephan, E.; Rocher, R.; Aubouet, J.; Pourcelot, G.; Cresson, P. Tetrahedron Asymm. 1993, 5, 41-44; Wu. M.-J.; Yeh, J.-Y. Tetrahedron 1994, 50, 1073-1082; Tsuge, H.; Takumi, K.; Nagai, T.; Okano, T.; Eguchi, S.; Kimoto, H. Tetrahedron 1997, 53, 823-838.
11. Review for asymmetric conjugate addition reaction: Tomioka, K.; Koga, K. in Asymmetric Synthesis Vol. 2, Academic Press, New York, 1983, chapter 7; Posner, G. H. ibid, chapter 8; Lutomoski, K. A.; Meyers, A. I. in Asymmetric Synthesis Vol. 3, Academic Press, New York, 1984, chapter 3; Oppolzer, W. Tetrahedron 1987,43, 1969-2004. Recent report: Oppolzer, W.; Poli, G.; Kingma, A. J.; Starkemann, C.; Bernardinelli, G. Helv. Chim. Acta 1987, 70, 2201-2214; Rück, K.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 694-696; Fang, C.-L.; Ogawa, T.; Suemune, H.; Sakai, K. Tetrahedron Asymm. 1991, 2, 389-398; Stephan, E.; Rocher, R.; Aubouet, J.; Pourcelot, G.; Cresson, P. Tetrahedron Asymm. 1993, 5, 41-44; Wu. M.-J.; Yeh, J.-Y. Tetrahedron 1994, 50, 1073-1082; Tsuge, H.; Takumi, K.; Nagai, T.; Okano, T.; Eguchi, S.; Kimoto, H. Tetrahedron 1997, 53, 823-838.
12. Tomioka, K.; Suenaga, T.; Koga, K. Tetrahedron Lett. 1986, 27, 369-372; Fleming, I.; Lawrence N. J. ibid. 1990, 31, 3645-3648; Didiuk, M. T.; Johannes, C. W.; Morken, J. P.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 7097-7104.
13. Tomioka, K.; Suenaga, T.; Koga, K. Tetrahedron Lett. 1986, 27, 369-372; Fleming, I.; Lawrence N. J. ibid. 1990, 31, 3645-3648; Didiuk, M. T.; Johannes, C. W.; Morken, J. P.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 7097-7104.
14. Tomioka, K.; Suenaga, T.; Koga, K. Tetrahedron Lett. 1986, 27, 369-372; Fleming, I.; Lawrence N. J. ibid. 1990, 31, 3645-3648; Didiuk, M. T.; Johannes, C. W.; Morken, J. P.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 7097-7104.
15. Tomioka, K. Synthesis 1990, 541-549.
16. Review for asymmetric reaction of organocopper: Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771-806; Kanai, M.; Nakagawa, Y.; Tomioka, K. J. Syn. Org. Chem. Jpn. 1996, 54, 474-480. Recent report: Nakagawa, Y.; Kanai, M.; Nagaoka, Y.; Tomioka, K. Tetrahedron Lett. 1996, 37, 7805-7808, and references cited therein.
17. Review for asymmetric reaction of organocopper: Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771-806; Kanai, M.; Nakagawa, Y.; Tomioka, K. J. Syn. Org. Chem. Jpn. 1996, 54, 474-480. Recent report: Nakagawa, Y.; Kanai, M.; Nagaoka, Y.; Tomioka, K. Tetrahedron Lett. 1996, 37, 7805-7808, and references cited therein.
18. Review for asymmetric reaction of organocopper: Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771-806; Kanai, M.; Nakagawa, Y.; Tomioka, K. J. Syn. Org. Chem. Jpn. 1996, 54, 474-480. Recent report: Nakagawa, Y.; Kanai, M.; Nagaoka, Y.; Tomioka, K. Tetrahedron Lett. 1996, 37, 7805-7808, and references cited therein.
19. Tomioka, K.; Shindo, M.; Koga, K. J. Am. Chem. Soc. 1989, 111, 8266-8268; Shindo, M.; Koga, K.; Tomioka, K. J. Am. Chem. Soc. 1992, 114, 8732-8733; Inoue, I.; Shindo, M.; Koga, K.; Kanai, M.; Tomioka, K. Tetrahedron Asymm. 1995, 6, 2527-2533; Fujieda, H.; Kanai, M.; Kambara, T.; Iida, A.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 2060-2061.
20. Tomioka, K.; Shindo, M.; Koga, K. J. Am. Chem. Soc. 1989, 111, 8266-8268; Shindo, M.; Koga, K.; Tomioka, K. J. Am. Chem. Soc. 1992, 114, 8732-8733; Inoue, I.; Shindo, M.; Koga, K.; Kanai, M.; Tomioka, K. Tetrahedron Asymm. 1995, 6, 2527-2533; Fujieda, H.; Kanai, M.; Kambara, T.; Iida, A.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 2060-2061.
21. Tomioka, K.; Shindo, M.; Koga, K. J. Am. Chem. Soc. 1989, 111, 8266-8268; Shindo, M.; Koga, K.; Tomioka, K. J. Am. Chem. Soc. 1992, 114, 8732-8733; Inoue, I.; Shindo, M.; Koga, K.; Kanai, M.; Tomioka, K. Tetrahedron Asymm. 1995, 6, 2527-2533; Fujieda, H.; Kanai, M.; Kambara, T.; Iida, A.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 2060-2061.
22. Tomioka, K.; Shindo, M.; Koga, K. J. Am. Chem. Soc. 1989, 111, 8266-8268; Shindo, M.; Koga, K.; Tomioka, K. J. Am. Chem. Soc. 1992, 114, 8732-8733; Inoue, I.; Shindo, M.; Koga, K.; Kanai, M.; Tomioka, K. Tetrahedron Asymm. 1995, 6, 2527-2533; Fujieda, H.; Kanai, M.; Kambara, T.; Iida, A.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 2060-2061.
23. Mizuno, M.; Kanai, M.; Iida, A.; Tomioka, K. Tetrahedron Asymm. 1996, 7, 2483-2484.
24. Tomioka, K.; Shindo, M.; Koga, K. Tetrahedron Lett. 1993, 34, 681-682.
25. Kretchmer, R. A. J. Org. Chem. 1972, 37, 2744-2747; Tsukazaki, M.; Tinkl, M.; Roglans, A.; Chapell, B. J.; Taylor, N. J.; Snieckus, V. J. Am. Chem. Soc. 1996, 118, 685-686; Weisenburger, G. A.; Beak, P. J. Am. Chem. Soc. 1996, 118, 12218-12219; Beak, P.; Basu, A.; Gallagher, D. J.; Park, Y. S.; Thayumanavan, S. Acc. Chem. Res. 1996, 29, 552-560.
26. Kretchmer, R. A. J. Org. Chem. 1972, 37, 2744-2747; Tsukazaki, M.; Tinkl, M.; Roglans, A.; Chapell, B. J.; Taylor, N. J.; Snieckus, V. J. Am. Chem. Soc. 1996, 118, 685-686; Weisenburger, G. A.; Beak, P. J. Am. Chem. Soc. 1996, 118, 12218-12219; Beak, P.; Basu, A.; Gallagher, D. J.; Park, Y. S.; Thayumanavan, S. Acc. Chem. Res. 1996, 29, 552-560.
27. Kretchmer, R. A. J. Org. Chem. 1972, 37, 2744-2747; Tsukazaki, M.; Tinkl, M.; Roglans, A.; Chapell, B. J.; Taylor, N. J.; Snieckus, V. J. Am. Chem. Soc. 1996, 118, 685-686; Weisenburger, G. A.; Beak, P. J. Am. Chem. Soc. 1996, 118, 12218-12219; Beak, P.; Basu, A.; Gallagher, D. J.; Park, Y. S.; Thayumanavan, S. Acc. Chem. Res. 1996, 29, 552-560.
28. Kretchmer, R. A. J. Org. Chem. 1972, 37, 2744-2747; Tsukazaki, M.; Tinkl, M.; Roglans, A.; Chapell, B. J.; Taylor, N. J.; Snieckus, V. J. Am. Chem. Soc. 1996, 118, 685-686; Weisenburger, G. A.; Beak, P. J. Am. Chem. Soc. 1996, 118, 12218-12219; Beak, P.; Basu, A.; Gallagher, D. J.; Park, Y. S.; Thayumanavan, S. Acc. Chem. Res. 1996, 29, 552-560.
29. Cooke, M. P. Jr. J. Org. Chem. 1986, 51, 1637-1638.
30. The Michael reaction of the initially formed lithium enolate with 3 is the major side reaction. The use of excess (3 eq) butyllithium prevents from this unfavorable side reaction.
31. Levene, P. A.; Marker, R. E. J. Biol. Chem. 1932, 95, 1-24.
32. Beak, P.; Meyers, A. I. Acc. Chem. Res. 1986, 29, 356-363.
33. Paquette, L. A.; Gilday, J. P. J. Org. Chem. 1988, 53, 4972-4978.
34. Meyers, A. I.; Smith, R. K.; Whitten, C. E. J. Org. Chem. 1979, 44, 2250-2256.
35. Mukaiyama, T.; Takeda, T.; Fujimoto, K. Bull. Chem. Soc. Jpn 1978, 51, 3368-3372.
36. Fang, C.-L.; Suemune, H.; Sakai, K. J. Org. Chem. 1992, 57, 4300-4303.
37. Schultz, A. G.; Macielag, M.; Podhorez, D. E.; Suhadolnik, J. C. J. Org. Chem. 1988, 53, 2456-2464.
38. 4).