exo- and Enantioselective Cycloaddition of Azomethine Ylides Generated from N-Alkylidene Glycine Esters Using Chiral Phosphine - Copper Complexes

Organic Letters

Volumn 5, Issue 26, 2003, Pages 5043-5046

  Oderaotoshi, Yoji ^a   Cheng, Wenji ^a   Fujitomi, Shintaro ^a   Kasano, Yukihiro ^a   Minakata, Satoshi ^a   Komatsu, Mitsuo ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AZOMETHINE YLIDE; COPPER COMPLEX; ESTER DERIVATIVE; GLYCINE DERIVATIVE; PHOSPHINE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHIRALITY; CYCLOADDITION; ENANTIOSELECTIVITY; REACTION ANALYSIS;

EID: 0347916937     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol036076s     Document Type: Article

References (33)

1. (a) Gribble, G. W. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.: Pergamon: Oxford, U.K., 1996; Vol. 2, pp 207-257.
2. (b) Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863-909.
3. (c) Lown, J. W. In 1,3-Dipolar Cycloaddition Chemistry; Padwa A., Ed.; John Wiley & Sons: New York, 1984; Vol. 1, pp 653-732.
4. Huisgen, R.; Scheer, W.; Huber, H. Tetrahedron Lett. 1966, 7, 397-464.
5. For examples, see: (a) Grigg, R.; Kemp, J. J. Chem. Soc., Chem. Commun. 1978, 109-111. (b) Grigg, R.; Donegan, G.; Gunaratne, H. Q. N. Tetrahedron 1989, 45, 1723-1746.
6. For examples, see: (a) Grigg, R.; Kemp, J. J. Chem. Soc., Chem. Commun. 1978, 109-111. (b) Grigg, R.; Donegan, G.; Gunaratne, H. Q. N. Tetrahedron 1989, 45, 1723-1746.
7. Huisgen, R.; Grashey, R. Tetrahedron Lett. 1963, 4, 1441-1445.
8. For examples, see: (a) Tsuge, O.; Kanemasa, S.; Yoshioka, M. J. Org. Chem. 1988, 53, 1384-1391. (b) Grigg, R.; Montgomery, J.; Somasunderam, A. Tetrahedron 1992, 48, 10431-10442.
9. For examples, see: (a) Tsuge, O.; Kanemasa, S.; Yoshioka, M. J. Org. Chem. 1988, 53, 1384-1391. (b) Grigg, R.; Montgomery, J.; Somasunderam, A. Tetrahedron 1992, 48, 10431-10442.
10. (a) Komatsu, M.; Okada, H.; Yokoi, S.; Minakata, S. Tetrahedron Lett. 2003, 44, 1603-1606.
11. (b) Okada, H.; Akaki, T.; Oderaotoshi, Y.; Minakata, S.; Komatsu, M. Tetrahedron 2003, 59, 197-205.
12. (c) Komatsu, M.; Okada, H.; Akaki, T.; Oderaotoshi, Y.; Minakata, S. Org. Lett. 2002, 4, 3505-3508.
13. (d) Ohno, M.; Komatsu, M.; Miyata, H.; Ohshiro, Y. Tetrahedron Lett. 1991, 32, 5813-5816.
14. (e) Komatsu, M.; Ohno, M.; Tsuno, S.; Ohshiro, Y. Chem. Lett. 1990, 575-576.
15. (f) Iyoda, M.; Sultana, F.; Kato, A.; Yoshida, M.; Kuwatani, Y.; Komatsu, M.; Nagase, S. Chem. Lett. 1997, 63-64.
16. (g) Iyoda, M.; Sultana, F.; Komatsu, M. Chem. Lett. 1995, 1133-1134.
17. (a) Komatsu, M.; Kasano, Y.; Yamaoka, S.; Minakata, S. Synthesis 2003, 1398-1402.
18. (b) Washizuka, K.-I.; Nagai, K.; Minakata, S.; Ryu, I.; Komatsu, M. Tetrahedron Lett. 2000, 41, 691-695.
19. (c) Washizuka, K.-I.; Minakata, S.; Ryu, I.; Komatsu, M. Tetrahedron 1999, 55, 12969-12976.
20. (d) Washizuka, K.-I.; Nagai, K.; Minakata, S.; Ryu, I.; Komatsu, M. Tetrahedron Lett. 1999, 40, 8849-8853.
21. (a) Allway, P.; Grigg, R. Tetrahedron Lett. 1991, 32, 5817-5820.
22. (b) Grigg, R. Tetrahedron: Asymmetry 1995, 6, 2475-2486.
23. (c) Gothelf, A. S.; Gothelf, K. V.; Hazell, R. G.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 4236-4238.
24. (d) Longmire, J. M.; Wang, B.; Zhang, X. J. Am. Chem. Soc. 2002, 124, 13400-13401.
25. (e) Chen, C.; Li, X.; Schreiber, S. L. J. Am. Chem. Soc. 2003, 125, 10174-10175.
26. A part of references of chiral phosphine ligands are as follows. CHIRAPHOS: Fryzuk, M. D.; Bosnish, B. J. Am. Chem. Soc. 1977, 99, 6262-6267. BDPP: MacNeil, P. A.; Roberts, N. K.; Bosnich, B. J. Am. Chem. Soc. 1981, 103, 2273-2280. DIOP: Dang, T. P.; Kagan, H. B. J. Chem. Soc., Chem. Commun. 1971, 481. BINAP: Miyashita, A.; Takeya, H.; Souchi, T.; Noyori R. Tetrahedron 1984, 40, 1245-1253. Tol-BINAP: Mashima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 9, 3064. H8-BINAP: Uemura, T.; Zhang, X.; Matsumura, K.; Sayo, N.; Kumobayashi, H.; Ohta, T.; Nozaki, K.; Takaya, H.; J. Org. Chem. 1996, 61, 5510. SEGPHOS: Saito, T.; Sayo, N.; Xiaoyaong, Z.; Yokozawa, T. Patent EP 0850945, 1998.
27. A part of references of chiral phosphine ligands are as follows. CHIRAPHOS: Fryzuk, M. D.; Bosnish, B. J. Am. Chem. Soc. 1977, 99, 6262-6267. BDPP: MacNeil, P. A.; Roberts, N. K.; Bosnich, B. J. Am. Chem. Soc. 1981, 103, 2273-2280. DIOP: Dang, T. P.; Kagan, H. B. J. Chem. Soc., Chem. Commun. 1971, 481. BINAP: Miyashita, A.; Takeya, H.; Souchi, T.; Noyori R. Tetrahedron 1984, 40, 1245-1253. Tol-BINAP: Mashima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 9, 3064. H8-BINAP: Uemura, T.; Zhang, X.; Matsumura, K.; Sayo, N.; Kumobayashi, H.; Ohta, T.; Nozaki, K.; Takaya, H.; J. Org. Chem. 1996, 61, 5510. SEGPHOS: Saito, T.; Sayo, N.; Xiaoyaong, Z.; Yokozawa, T. Patent EP 0850945, 1998.
28. A part of references of chiral phosphine ligands are as follows. CHIRAPHOS: Fryzuk, M. D.; Bosnish, B. J. Am. Chem. Soc. 1977, 99, 6262-6267. BDPP: MacNeil, P. A.; Roberts, N. K.; Bosnich, B. J. Am. Chem. Soc. 1981, 103, 2273-2280. DIOP: Dang, T. P.; Kagan, H. B. J. Chem. Soc., Chem. Commun. 1971, 481. BINAP: Miyashita, A.; Takeya, H.; Souchi, T.; Noyori R. Tetrahedron 1984, 40, 1245-1253. Tol-BINAP: Mashima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 9, 3064. H8-BINAP: Uemura, T.; Zhang, X.; Matsumura, K.; Sayo, N.; Kumobayashi, H.; Ohta, T.; Nozaki, K.; Takaya, H.; J. Org. Chem. 1996, 61, 5510. SEGPHOS: Saito, T.; Sayo, N.; Xiaoyaong, Z.; Yokozawa, T. Patent EP 0850945, 1998.
29. A part of references of chiral phosphine ligands are as follows. CHIRAPHOS: Fryzuk, M. D.; Bosnish, B. J. Am. Chem. Soc. 1977, 99, 6262-6267. BDPP: MacNeil, P. A.; Roberts, N. K.; Bosnich, B. J. Am. Chem. Soc. 1981, 103, 2273-2280. DIOP: Dang, T. P.; Kagan, H. B. J. Chem. Soc., Chem. Commun. 1971, 481. BINAP: Miyashita, A.; Takeya, H.; Souchi, T.; Noyori R. Tetrahedron 1984, 40, 1245-1253. Tol-BINAP: Mashima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 9, 3064. H8-BINAP: Uemura, T.; Zhang, X.; Matsumura, K.; Sayo, N.; Kumobayashi, H.; Ohta, T.; Nozaki, K.; Takaya, H.; J. Org. Chem. 1996, 61, 5510. SEGPHOS: Saito, T.; Sayo, N.; Xiaoyaong, Z.; Yokozawa, T. Patent EP 0850945, 1998.
30. A part of references of chiral phosphine ligands are as follows. CHIRAPHOS: Fryzuk, M. D.; Bosnish, B. J. Am. Chem. Soc. 1977, 99, 6262-6267. BDPP: MacNeil, P. A.; Roberts, N. K.; Bosnich, B. J. Am. Chem. Soc. 1981, 103, 2273-2280. DIOP: Dang, T. P.; Kagan, H. B. J. Chem. Soc., Chem. Commun. 1971, 481. BINAP: Miyashita, A.; Takeya, H.; Souchi, T.; Noyori R. Tetrahedron 1984, 40, 1245-1253. Tol-BINAP: Mashima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 9, 3064. H8-BINAP: Uemura, T.; Zhang, X.; Matsumura, K.; Sayo, N.; Kumobayashi, H.; Ohta, T.; Nozaki, K.; Takaya, H.; J. Org. Chem. 1996, 61, 5510. SEGPHOS: Saito, T.; Sayo, N.; Xiaoyaong, Z.; Yokozawa, T. Patent EP 0850945, 1998.
31. A part of references of chiral phosphine ligands are as follows. CHIRAPHOS: Fryzuk, M. D.; Bosnish, B. J. Am. Chem. Soc. 1977, 99, 6262-6267. BDPP: MacNeil, P. A.; Roberts, N. K.; Bosnich, B. J. Am. Chem. Soc. 1981, 103, 2273-2280. DIOP: Dang, T. P.; Kagan, H. B. J. Chem. Soc., Chem. Commun. 1971, 481. BINAP: Miyashita, A.; Takeya, H.; Souchi, T.; Noyori R. Tetrahedron 1984, 40, 1245-1253. Tol-BINAP: Mashima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 9, 3064. H8-BINAP: Uemura, T.; Zhang, X.; Matsumura, K.; Sayo, N.; Kumobayashi, H.; Ohta, T.; Nozaki, K.; Takaya, H.; J. Org. Chem. 1996, 61, 5510. SEGPHOS: Saito, T.; Sayo, N.; Xiaoyaong, Z.; Yokozawa, T. Patent EP 0850945, 1998.
32. A part of references of chiral phosphine ligands are as follows. CHIRAPHOS: Fryzuk, M. D.; Bosnish, B. J. Am. Chem. Soc. 1977, 99, 6262-6267. BDPP: MacNeil, P. A.; Roberts, N. K.; Bosnich, B. J. Am. Chem. Soc. 1981, 103, 2273-2280. DIOP: Dang, T. P.; Kagan, H. B. J. Chem. Soc., Chem. Commun. 1971, 481. BINAP: Miyashita, A.; Takeya, H.; Souchi, T.; Noyori R. Tetrahedron 1984, 40, 1245-1253. Tol-BINAP: Mashima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 9, 3064. H8-BINAP: Uemura, T.; Zhang, X.; Matsumura, K.; Sayo, N.; Kumobayashi, H.; Ohta, T.; Nozaki, K.; Takaya, H.; J. Org. Chem. 1996, 61, 5510. SEGPHOS: Saito, T.; Sayo, N.; Xiaoyaong, Z.; Yokozawa, T. Patent EP 0850945, 1998.
33. The method is in Cache ver. 4.0 program (Fujitsu Corporation).