Intermolecular 1,3-dipolar cycloaddition of chiral and geometry fixed α-alkoxycarbonylnitrone, 5,6-dihydro-5-phenyl-2H-1,4-oxazin-2-one N-oxide

Chemical Communications

Volumn , Issue 16, 1996, Pages 1861-1862

  Tamura, Osamu ^a   Gotanda, Kentoku ^a   Terashima, Romi ^a   Kikuchi, Mayumi ^a   Miyawaki, Tsutomu ^a   Sakamoto, Masanori ^a  

^a MEIJI PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000460570     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/CC9960001861     Document Type: Article

References (20)

1. For general reviews for nitrone cycloadditions see: P. N. Confalone and E. M, Huie, Org. React., 1988, 36, 1; W. Carruthers, Cycloaddition Reactions in Organic Synthesis, Pergamon, Oxford, 1990, pp. 269-331.
2. For general reviews for nitrone cycloadditions see: P. N. Confalone and E. M, Huie, Org. React., 1988, 36, 1; W. Carruthers, Cycloaddition Reactions in Organic Synthesis, Pergamon, Oxford, 1990, pp. 269-331.
3. (a) J. Hara, Y. Inouye and H. Kakisawa, Bull. Chem. Soc. Jpn., 1981, 54, 3871;
4. (b) H. Iida, K. Kasahara and C. Kibayashi, J. Am. Chem. Soc., 1986, 108, 4647; K. Kasahara, H. Iida and C. Kibayashi, J. Org. Chem., 1989, 54, 2225; See also, A. Vasella, R. Voeffray, J. Pless and R. Huguenin, Helv. Chim. Acta, 1983, 66, 1241 and references cited therein;
5. (b) H. Iida, K. Kasahara and C. Kibayashi, J. Am. Chem. Soc., 1986, 108, 4647; K. Kasahara, H. Iida and C. Kibayashi, J. Org. Chem., 1989, 54, 2225; See also, A. Vasella, R. Voeffray, J. Pless and R. Huguenin, Helv. Chim. Acta, 1983, 66, 1241 and references cited therein;
6. (b) H. Iida, K. Kasahara and C. Kibayashi, J. Am. Chem. Soc., 1986, 108, 4647; K. Kasahara, H. Iida and C. Kibayashi, J. Org. Chem., 1989, 54, 2225; See also, A. Vasella, R. Voeffray, J. Pless and R. Huguenin, Helv. Chim. Acta, 1983, 66, 1241 and references cited therein;
7. (c) M. Ito, C. Kibayashi, Tetrahedron Lett., 1990, 31, 5065;
8. (d) T. Kametani, S.-D. Chu and T. Honda, J. Chem. Soc., Perkin Trans. I, 1988, 1593.
9. Y. Inouye, J. Hara and H. Kakisawa, Chem. Lett., 1980, 1407; Y. Inouye, Bull. Chem. Soc. Jpn., 1983, 56, 244; Y. Inouye, K. Takaya and H. Kakisawa, Bull. Chem. Soc. Jpn., 1983, 56, 3541; H. G. Aurich, M. Franzke and H. P. Kesselheim, Tetrahedron, 1992, 48, 663.
10. Y. Inouye, J. Hara and H. Kakisawa, Chem. Lett., 1980, 1407; Y. Inouye, Bull. Chem. Soc. Jpn., 1983, 56, 244; Y. Inouye, K. Takaya and H. Kakisawa, Bull. Chem. Soc. Jpn., 1983, 56, 3541; H. G. Aurich, M. Franzke and H. P. Kesselheim, Tetrahedron, 1992, 48, 663.
11. Y. Inouye, J. Hara and H. Kakisawa, Chem. Lett., 1980, 1407; Y. Inouye, Bull. Chem. Soc. Jpn., 1983, 56, 244; Y. Inouye, K. Takaya and H. Kakisawa, Bull. Chem. Soc. Jpn., 1983, 56, 3541; H. G. Aurich, M. Franzke and H. P. Kesselheim, Tetrahedron, 1992, 48, 663.
12. Y. Inouye, J. Hara and H. Kakisawa, Chem. Lett., 1980, 1407; Y. Inouye, Bull. Chem. Soc. Jpn., 1983, 56, 244; Y. Inouye, K. Takaya and H. Kakisawa, Bull. Chem. Soc. Jpn., 1983, 56, 3541; H. G. Aurich, M. Franzke and H. P. Kesselheim, Tetrahedron, 1992, 48, 663.
13. C. Belzecki and I. Panfil, J. Org. Chem., 1979, 44, 1212.
14. Recently, related 5-membered ring nitrones have been reported, see (a) N. Katagiri, H. Sato, A. Kurimoto, M. Okada, A. Yamada and C. Kaneko, J. Org. Chem., 1994, 59, 8101. Related cyclic azomethynilides have been reported; (b) L. M. Harwood and I. A. Lilley, Tetrahedron Lett.. 1993, 34, 537 and references cited therein; (c) R. M. Williams, W. Zhai, D. J. Aldous and S. C. Aldous, J. Org. Chem., 1992, 57, 6527.
15. Recently, related 5-membered ring nitrones have been reported, see (a) N. Katagiri, H. Sato, A. Kurimoto, M. Okada, A. Yamada and C. Kaneko, J. Org. Chem., 1994, 59, 8101. Related cyclic azomethynilides have been reported; (b) L. M. Harwood and I. A. Lilley, Tetrahedron Lett.. 1993, 34, 537 and references cited therein; (c) R. M. Williams, W. Zhai, D. J. Aldous and S. C. Aldous, J. Org. Chem., 1992, 57, 6527.
16. Recently, related 5-membered ring nitrones have been reported, see (a) N. Katagiri, H. Sato, A. Kurimoto, M. Okada, A. Yamada and C. Kaneko, J. Org. Chem., 1994, 59, 8101. Related cyclic azomethynilides have been reported; (b) L. M. Harwood and I. A. Lilley, Tetrahedron Lett.. 1993, 34, 537 and references cited therein; (c) R. M. Williams, W. Zhai, D. J. Aldous and S. C. Aldous, J. Org. Chem., 1992, 57, 6527.
17. T. Polonski and A. Chimiak, Tetrahedron Lett., 1974, 2453.
18. Sk. A. Ali and M. M. Wazeer, J. Chem. Soc., Perkin Trans. 2, 1986, 1789.
19. W. H. Pirkle, M. H. Hyun and B. Bank, J. Chramatogr., 1984, 316, 585; W. H. Pirkle and T. C. Pochapsky, J. Am. Chem. Soc., 1986, 108, 352.
20. W. H. Pirkle, M. H. Hyun and B. Bank, J. Chramatogr., 1984, 316, 585; W. H. Pirkle and T. C. Pochapsky, J. Am. Chem. Soc., 1986, 108, 352.