Catalytic Asymmetric Iodocarbocyclization Reaction of 4-Alkenylmalonates and Its Application to Enantiotopic Group Selective Reaction

Journal of Organic Chemistry

Volumn 62, Issue 21, 1997, Pages 7384-7389

  Inoue, Tadashi ^a   Kitagawa, Osamu ^a   Saito, Akio ^a   Taguchi, Takeo ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000279657     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970970d     Document Type: Article

References (44)

1. (a) Morrison, J. D., Ed. Asymmetric Synthesis, Academic Press: New York, 1985; Vol. 5.
2. (b) Narasaka, K. Synthesis 1990, 1-11.
3. (c) Noyori, R. Asymmetric Catalysis in Organic Synthesis, John Wiley: New York, 1994.
4. (a) Bougalt, M. J. C. R. Hebd. Seances Acad. Sci. 1904, 139, 864-870.
5. (b) Bartlett, P. A. Asymmetric Synthesis, Morrison, J. D., Ed.; Academic Press: Orland, 1984; Vol. 4, Chapter 6, p 411-453.
6. (c) Gardillo, G.; Orena, M. Tetrahedron 1990, 46, 3321-3408.
7. (a) Kitagawa, O.; Inoue, T.; Taguchi, T. Tetrahedron Lett. 1992, 33, 2167-2170.
8. (b) Kitagawa, O.; Inoue, T.; Hirano, K.; Taguchi, T. J. Org. Chem. 1993, 58, 3106-3112.
9. (c) Kitagawa, O.; Inoue, T.; Taguchi, T. Tetrahedron Lett. 1994, 35, 1059-1062.
10. (d) Inoue, T.; Kitagawa, O.; Oda, Y.; Taguchi, T. J. Org. Chem. 1996, 61, 8256-8263.
11. (e) Taguchi, T.; Kitagawa, O.; Inoue, T. J. Synth. Org. Chem. Jpn. 1995, 53, 770-779.
12. (f) Kitagawa, O.; Inoue, T.; Taguchi, T. Rev. Heteroatom Chem. 1996, 15, 243-262.
13. Examples of NaH-mediated iodocarbocyclization reaction of active methine or methylene compounds: (a) Cossy, J.; Thellend, A. Tetrahedron Lett. 1990, 31, 1427-1428.
14. (b) Beckwith, A. L.; Zozer, M. J. Tetrahedron Lett. 1992, 33, 4975-4978.
15. Inoue, T.; Kitagawa, O.; Ochiai, O.; Taguchi, T. Tetrahedron: Asymmetry 1995, 6, 691-692.
16. Preliminary communication of this work: (a) Inoue, T.; Kitagawa, O.; Kurumizawa, S.; Ochiai, O.; Taguchi, T. Tetrahedron Lett. 1995, 36, 1479-1482.
17. (b) Inoue, T.; Kitagawa, O.; Ochiai, O.; Shiro, M.; Taguchi, T. Tetrahedron Lett. 1995, 36, 9333-1112.
18. (a) Narasaka, K.; Inoue, M.; Okada, N. Chem. Lett. 1986, 1109-1112.
19. (b) Seebach, D.; Beck, A. K.; Imwinkelreid, R.; Roggo, S.; Wonnacott, A. Helv. Chim. Acta 1987, 70, 954-974.
20. (c) Narasaka, K.; Iwasawa, N. Organic Synthesis Theory and Applications; Hudlicky, T., Ed.; JAI Press Inc.: London, 1993; p 93-112.
21. (d) Dahinden, R.; Beck, A.; K. Seebach, D. Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: Chichester, 1994; Vol. 3, pp 2167-2170.
22. (a) Schmidt, B.; Seebach, D. Angew. Chem. Int. Ed. Engl. 1991, 30, 99-100.
23. (b) Seebach, D.; Behrendt, L.; Felix, D. Angew. Chem. Int. Ed. Engl. 1991, 30, 1008-1009.
24. 2O.
25. 4 having no activity as a base, the reaction gave only a complex mixture.
26. 3N.
27. In the present reaction, the use of THF as a solvent resulted in the decrease in both enantioselectivity and yield (85% ee, 34%).
28. In the reaction of 1e, complete lactonization to 3e from 2e was observed even at -78°C.
29. Jakovac, I. J.; Goodbrand, H. B.; Lok, K. P.; Jones, J. B. J. Am. Chem. Soc. 1982, 104, 4659-4665.
30. Examples of the catalytic asymmetric synthesis of cyclopentanoid compounds: (a) Sato, Y.; Honda, T.; Shibasaki, M. Tetrahedron Lett. 1992, 33, 2593-2596. (b) Wu, X. M.; Funakoshi, K.; Sakai, K. Tetrahedron Lett. 1993, 34, 5927-5930. (c) Sato, Y.; Mori, M.; Shibasaki, M. Tetrahedron: Asymmetry 1995, 6, 757-766. (d) Ohshima, T.; Kagechika, K.; Adachi, M.; Sodeoka, M.; Shibasaki, M. J. Am. Chem. Soc. 1996, 118, 7108-7116.
31. Examples of the catalytic asymmetric synthesis of cyclopentanoid compounds: (a) Sato, Y.; Honda, T.; Shibasaki, M. Tetrahedron Lett. 1992, 33, 2593-2596. (b) Wu, X. M.; Funakoshi, K.; Sakai, K. Tetrahedron Lett. 1993, 34, 5927-5930. (c) Sato, Y.; Mori, M.; Shibasaki, M. Tetrahedron: Asymmetry 1995, 6, 757-766. (d) Ohshima, T.; Kagechika, K.; Adachi, M.; Sodeoka, M.; Shibasaki, M. J. Am. Chem. Soc. 1996, 118, 7108-7116.
32. Examples of the catalytic asymmetric synthesis of cyclopentanoid compounds: (a) Sato, Y.; Honda, T.; Shibasaki, M. Tetrahedron Lett. 1992, 33, 2593-2596. (b) Wu, X. M.; Funakoshi, K.; Sakai, K. Tetrahedron Lett. 1993, 34, 5927-5930. (c) Sato, Y.; Mori, M.; Shibasaki, M. Tetrahedron: Asymmetry 1995, 6, 757-766. (d) Ohshima, T.; Kagechika, K.; Adachi, M.; Sodeoka, M.; Shibasaki, M. J. Am. Chem. Soc. 1996, 118, 7108-7116.
33. Examples of the catalytic asymmetric synthesis of cyclopentanoid compounds: (a) Sato, Y.; Honda, T.; Shibasaki, M. Tetrahedron Lett. 1992, 33, 2593-2596. (b) Wu, X. M.; Funakoshi, K.; Sakai, K. Tetrahedron Lett. 1993, 34, 5927-5930. (c) Sato, Y.; Mori, M.; Shibasaki, M. Tetrahedron: Asymmetry 1995, 6, 757-766. (d) Ohshima, T.; Kagechika, K.; Adachi, M.; Sodeoka, M.; Shibasaki, M. J. Am. Chem. Soc. 1996, 118, 7108-7116.
34. (a) Ward, R. S. Chem. Soc. Rev. 1990, 19, 1.
35. (b) Mikami, K.; Narisawa, S.; Shimizu, M.; Terada, M. J. Am. Chem. Soc. 1992, 114, 6566-6568.
36. The relative configurations of cis-3f, cis-3g, and trans-3h were determined on the basis of NOE experiments.
37. Sakan, T.; Murai, Y.; Hayashi, Y.; Honda, Y.; Shono, T.; Nakajima, M.; Kato, M. Tetrahedron 1967, 23, 4635-4652.
38. Examples of asymmetric synthesis of boschnialactone; (a) Arai, Y.; Kawanami, S.; Koizumi, T. Chem. Lett. 1990, 1585-1586. (b) Arai, Y.; Kawanami, S.; Koizumi, T. J. Chem. Soc., Perkin Trans. 1 1991, 2969-2975. (c) Tanaka, D.; Yoshino, T.; Kouno, I.; Miyashita, M.; Irie, H. Tetrahedron 1993, 49, 10253-10262. (d) Nangia, A.; Prasuna, G.; Bheema Rao, P. Tetrahedron Lett. 1994, 35, 3755-3758.
39. Examples of asymmetric synthesis of boschnialactone; (a) Arai, Y.; Kawanami, S.; Koizumi, T. Chem. Lett. 1990, 1585-1586. (b) Arai, Y.; Kawanami, S.; Koizumi, T. J. Chem. Soc., Perkin Trans. 1 1991, 2969-2975. (c) Tanaka, D.; Yoshino, T.; Kouno, I.; Miyashita, M.; Irie, H. Tetrahedron 1993, 49, 10253-10262. (d) Nangia, A.; Prasuna, G.; Bheema Rao, P. Tetrahedron Lett. 1994, 35, 3755-3758.
40. Examples of asymmetric synthesis of boschnialactone; (a) Arai, Y.; Kawanami, S.; Koizumi, T. Chem. Lett. 1990, 1585-1586. (b) Arai, Y.; Kawanami, S.; Koizumi, T. J. Chem. Soc., Perkin Trans. 1 1991, 2969-2975. (c) Tanaka, D.; Yoshino, T.; Kouno, I.; Miyashita, M.; Irie, H. Tetrahedron 1993, 49, 10253-10262. (d) Nangia, A.; Prasuna, G.; Bheema Rao, P. Tetrahedron Lett. 1994, 35, 3755-3758.
41. Examples of asymmetric synthesis of boschnialactone; (a) Arai, Y.; Kawanami, S.; Koizumi, T. Chem. Lett. 1990, 1585-1586. (b) Arai, Y.; Kawanami, S.; Koizumi, T. J. Chem. Soc., Perkin Trans. 1 1991, 2969-2975. (c) Tanaka, D.; Yoshino, T.; Kouno, I.; Miyashita, M.; Irie, H. Tetrahedron 1993, 49, 10253-10262. (d) Nangia, A.; Prasuna, G.; Bheema Rao, P. Tetrahedron Lett. 1994, 35, 3755-3758.
42. (a) Labelle, M.; Morton, H. E.; Guindon, Y.; Springler, J. P. J. Am. Chem. Soc. 1988, 110, 4533-4540.
43. (b) Labelle, M.; Guindon, Y. J. Am. Chem. Soc. 1989, 11, 2204-2210.
44. Sato, T.; Ito, D.; Kuki, M.; Tanaka, H.; Ota, T. Macromolecules 1991, 24, 2963-2967.