Lewis acid-catalyzed asymmetric hetero Diels-Alder cycloaddition of a 1-thiabuta-1,3-diene with chiral N-acryloyl- and N-crotonoyl-oxazolidinone dienophiles

Tetrahedron Letters

Volumn 38, Issue 34, 1997, Pages 6035-6038

  Saito, Takao ^a   Suda, Hirofumi ^a   Kawamura, Mikako ^a   Nishimura, Jun Ichi ^a   Yamaya, Akemi ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

OXAZOLIDINONE DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

BETULACEAE;

EID: 0030785758     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01354-3     Document Type: Article

References (22)

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4. Oppolzer W.; Weinreb, S. M.; Boger, D. L.; Roush W. R.; Sweger, R. W.; Czarnik A. W. In Comprehensive Organic Synthesis, Ed., Trost, B. M., Fleming, I. and Paquett, L. A. Pergamon Press, Oxford, 1991, Vol. 5, p. 315, 401, 451, 513 and 551; Bednarski, M. D. and Lyssikatos, J. P. In Comprehensive Organic Synthesis, Ed., Trost, B. M., Fleming, I. and Paquett, L. A. Pergamon Press, Oxford, 1991, Vol. 2, p. 661; Kagan, H. B. and Riant O. Chem. Rev., 1992, 92, 1007; Waldmann, H. Synthesis, 1994, 535; Streith, J.; Defoin, A. Synthesis, 1994, 1107; Kametani, T.; Hibino, S. Adv. Heterocycl. Chem., 1987, 42, 245.
5. Oppolzer W.; Weinreb, S. M.; Boger, D. L.; Roush W. R.; Sweger, R. W.; Czarnik A. W. In Comprehensive Organic Synthesis, Ed., Trost, B. M., Fleming, I. and Paquett, L. A. Pergamon Press, Oxford, 1991, Vol. 5, p. 315, 401, 451, 513 and 551; Bednarski, M. D. and Lyssikatos, J. P. In Comprehensive Organic Synthesis, Ed., Trost, B. M., Fleming, I. and Paquett, L. A. Pergamon Press, Oxford, 1991, Vol. 2, p. 661; Kagan, H. B. and Riant O. Chem. Rev., 1992, 92, 1007; Waldmann, H. Synthesis, 1994, 535; Streith, J.; Defoin, A. Synthesis, 1994, 1107; Kametani, T.; Hibino, S. Adv. Heterocycl. Chem., 1987, 42, 245.
6. Oppolzer W.; Weinreb, S. M.; Boger, D. L.; Roush W. R.; Sweger, R. W.; Czarnik A. W. In Comprehensive Organic Synthesis, Ed., Trost, B. M., Fleming, I. and Paquett, L. A. Pergamon Press, Oxford, 1991, Vol. 5, p. 315, 401, 451, 513 and 551; Bednarski, M. D. and Lyssikatos, J. P. In Comprehensive Organic Synthesis, Ed., Trost, B. M., Fleming, I. and Paquett, L. A. Pergamon Press, Oxford, 1991, Vol. 2, p. 661; Kagan, H. B. and Riant O. Chem. Rev., 1992, 92, 1007; Waldmann, H. Synthesis, 1994, 535; Streith, J.; Defoin, A. Synthesis, 1994, 1107; Kametani, T.; Hibino, S. Adv. Heterocycl. Chem., 1987, 42, 245.
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13. For examples of Lewis acid-dependent reversal of facial selectivity, see Tietze, L. F.; Schneider, C.; Montenbruck, A. Angew. Chem. Int. Ed. Engl. 1994, 33, 980; Denmark, S. E.; Schnute, M. E. J. Org. Chem., 1991, 56, 6738; Amoroso, R.; Cardillo, G.; Sabatino, P.; Tomasini, C.; Trere, A. J. Org. Chem., 1933, 58, 5615;Waldmann, H. J. Org. Chem., 1988, 53, 6133; Poll, T.; Sobczak, A.; Hartmann, H.; Helmchen, G. Tetrahedron Lett., 1985, 26, 3095;
14. For examples of Lewis acid-dependent reversal of facial selectivity, see Tietze, L. F.; Schneider, C.; Montenbruck, A. Angew. Chem. Int. Ed. Engl. 1994, 33, 980; Denmark, S. E.; Schnute, M. E. J. Org. Chem., 1991, 56, 6738; Amoroso, R.; Cardillo, G.; Sabatino, P.; Tomasini, C.; Trere, A. J. Org. Chem., 1933, 58, 5615; Waldmann, H. J. Org. Chem., 1988, 53, 6133; Poll, T.; Sobczak, A.; Hartmann, H.; Helmchen, G. Tetrahedron Lett., 1985, 26, 3095;
15. For examples of Lewis acid-dependent reversal of facial selectivity, see Tietze, L. F.; Schneider, C.; Montenbruck, A. Angew. Chem. Int. Ed. Engl. 1994, 33, 980; Denmark, S. E.; Schnute, M. E. J. Org. Chem., 1991, 56, 6738; Amoroso, R.; Cardillo, G.; Sabatino, P.; Tomasini, C.; Trere, A. J. Org. Chem., 1933, 58, 5615; Waldmann, H. J. Org. Chem., 1988, 53, 6133; Poll, T.; Sobczak, A.; Hartmann, H.; Helmchen, G. Tetrahedron Lett., 1985, 26, 3095;
16. For examples of Lewis acid-dependent reversal of facial selectivity, see Tietze, L. F.; Schneider, C.; Montenbruck, A. Angew. Chem. Int. Ed. Engl. 1994, 33, 980; Denmark, S. E.; Schnute, M. E. J. Org. Chem., 1991, 56, 6738; Amoroso, R.; Cardillo, G.; Sabatino, P.; Tomasini, C.; Trere, A. J. Org. Chem., 1933, 58, 5615; Waldmann, H. J. Org. Chem., 1988, 53, 6133; Poll, T.; Sobczak, A.; Hartmann, H.; Helmchen, G. Tetrahedron Lett., 1985, 26, 3095;
17. For examples of Lewis acid-dependent reversal of facial selectivity, see Tietze, L. F.; Schneider, C.; Montenbruck, A. Angew. Chem. Int. Ed. Engl. 1994, 33, 980; Denmark, S. E.; Schnute, M. E. J. Org. Chem., 1991, 56, 6738; Amoroso, R.; Cardillo, G.; Sabatino, P.; Tomasini, C.; Trere, A. J. Org. Chem., 1933, 58, 5615; Waldmann, H. J. Org. Chem., 1988, 53, 6133; Poll, T.; Sobczak, A.; Hartmann, H.; Helmchen, G. Tetrahedron Lett., 1985, 26, 3095;
18. 4-N-acyloxazolidinone complexation, see Castellino, S. J. Org. Chem., 1990, 55, 5197.
19. 4-N-acyloxazolidinone complexation, see Castellino, S. J. Org. Chem., 1990, 55, 5197.
20. 4-N-acyloxazolidinone complexation, see Castellino, S. J. Org. Chem., 1990, 55, 5197.
21. For related observations in carbo Diels-Alder reaction, see Kadota, I.; Kobayashi, K.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Chem. Commun., 1995, 1271; and references cited therein.
22. ,2,3.