An efficient synthesis of (pyrrolidin-2-ylidene)glycinate using intramolecular 1, 3-dipolar cycloaddition of azide and olefin

Tetrahedron

Volumn 55, Issue 44, 1999, Pages 12723-12740

  Konda, Yaeko ^a   Sato, Takahiro ^a   Tsushima, Kaori ^a   Dodo, Masataka ^a   Kusunoki, Ami ^a   Sakayanagi, Masataka ^a   Sato, Noriko ^a   Takeda, Kazuyoshi ^b   Harigaya, Yoshihiro ^a  

^a KITASATO UNIVERSITY   (Japan)

^b EBARA CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

(2 PYRROLIDINYLIDENE)GLYCINATE; ALKENE; AZIDE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CANCER CHEMOTHERAPY; CYCLIZATION; DRUG SYNTHESIS; ISOMERISM; MASS SPECTROMETRY; MOLECULAR INTERACTION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

STAPHYLOCOCCUS PHAGE 3A;

EID: 0033615755     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00753-X     Document Type: Article

References (23)

1. a) Hata, T.; Koga, F.; Kanamori, K.; Matsumae, A.; Sugawara, R.; Shima, T.; Ito, S.; Tomizawa, S. J. Antibiot. Ser. A 1954, 7, 107.
2. b) Nagaoka, K.; Matsumoto, M.; Oono, J., Yokoi, K.; Ishizeki, S.; Nakashima, T. J. Antibiotics 1986, 39, 1527., Yokoi, K.; Nagaoka, K.; Nakashima, T. Chem. Pharm. Bull. 1986, 34, 4554.
3. b) Nagaoka, K.; Matsumoto, M.; Oono, J., Yokoi, K.; Ishizeki, S.; Nakashima, T. J. Antibiotics 1986, 39, 1527., Yokoi, K.; Nagaoka, K.; Nakashima, T. Chem. Pharm. Bull. 1986, 34, 4554.
4. Moran, E. J.; Armstrong, R. W. Tetrahedron Lett. 1991, 32, 3807.
5. Coleman R. S.; Kong, J. S. J. Am. Chem. Soc. 1998, 120, 3538.
6. a) Huisgen, R. Angew. Chem. 1963, 75, 604, 742., Angew Chem., Int. Ed. Eng. 1963, 2, 565, 633., Huisgen, R. J. Org. Chem. 1968, 33, 2291.
7. a) Huisgen, R. Angew. Chem. 1963, 75, 604, 742., Angew Chem., Int. Ed. Eng. 1963, 2, 565, 633., Huisgen, R. J. Org. Chem. 1968, 33, 2291.
8. a) Huisgen, R. Angew. Chem. 1963, 75, 604, 742., Angew Chem., Int. Ed. Eng. 1963, 2, 565, 633., Huisgen, R. J. Org. Chem. 1968, 33, 2291.
9. b) Smith, P. A. S.; Shang-Shing, P. C. J. Org. Chem. 1981, 46, 3970.
10. c) Buchanan, J. G.; Edgar, A. R.; Hewitt, B. D. J. Chem. Soc. Perkin Trans. 1, 1987, 2371.
11. d) Logothetis, A. L. J. Am. Chem. Soc. 1965, 87 (4) 749., Liu, J. M. L.; Young, J. J.; Li, Y. J.; Sha, C. K. J. Org. Chem., 1986, 51, 1120, Young J. J.; Sha, C. K. Heterocycles, 1984, 22 (11) 2571.; Hassner, A.; Amarasekara, A. S.; Andisik D. J. Org. Chem. 1988, 53, 27.
12. d) Logothetis, A. L. J. Am. Chem. Soc. 1965, 87 (4) 749., Liu, J. M. L.; Young, J. J.; Li, Y. J.; Sha, C. K. J. Org. Chem., 1986, 51, 1120, Young J. J.; Sha, C. K. Heterocycles, 1984, 22 (11) 2571.; Hassner, A.; Amarasekara, A. S.; Andisik D. J. Org. Chem. 1988, 53, 27.
13. d) Logothetis, A. L. J. Am. Chem. Soc. 1965, 87 (4) 749., Liu, J. M. L.; Young, J. J.; Li, Y. J.; Sha, C. K. J. Org. Chem., 1986, 51, 1120, Young J. J.; Sha, C. K. Heterocycles, 1984, 22 (11) 2571.; Hassner, A.; Amarasekara, A. S.; Andisik D. J. Org. Chem. 1988, 53, 27.
14. d) Logothetis, A. L. J. Am. Chem. Soc. 1965, 87 (4) 749., Liu, J. M. L.; Young, J. J.; Li, Y. J.; Sha, C. K. J. Org. Chem., 1986, 51, 1120, Young J. J.; Sha, C. K. Heterocycles, 1984, 22 (11) 2571.; Hassner, A.; Amarasekara, A. S.; Andisik D. J. Org. Chem. 1988, 53, 27.
15. Bernardi, R.; Ghiringhelli, D. J. Org. Chem. 1987, 52, 5021.
16. Schmidt, U.; Lieberknecht, A. W. Synthesis, 1984, 53.
17. Natsumori, N.; Murata, M.; Tachibana, K. Tetrahedron 1995, 51, 12229.
18. Kenner, J.; Richards, G. N. J. Chem. Soc. 1957, 3019.
19. Schmidt, U.; Ghirighhelli D. J. Org. Chem. 1987, 52, 5021.
20. Berkowitz, D. B.; Eggen, M.; Shen, Q.; Shoemaker, P. K. J. Org. Chem. 1996, 61, 4666.
21. Kolsaker, P.; Ellingsen, P.O.; Woien, G. Acta Chem. Scand. B 1973, 32, 683
22. Intramolecular 1,3-dipolar cycloadditions. Wade, P. A., In Conprehensive Organic Synthesis, Semmelhack M. F., Editor; Pergamon Press, Vol 4, Chapter 4, p 1157.
23. Konda, Y.; Machida, T.; Akaiwa, M.; Takeda, K.; Harigaya, Y. Heterocycles 1996, 43 (3) 560.