Tandem Inter [4 + 2]/Intra [3 + 2] Cycloadditions. 17. The Spiro Mode. Efficient and Highly Selective Synthesis of Azapropellanes

Journal of Organic Chemistry

Volumn 63, Issue 5, 1998, Pages 1604-1618

  Denmark, Scott E ^a   Middleton, Donald S ^a,b  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000425787     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9719057     Document Type: Article

References (35)

1. (a) Ho, T.-L. Tandem Organic Reactions; Wiley: New York, 1992.
2. (b) Ziegler, F. E. In Comprehensive Organic Synthesis, Combining C-C π-Bonds; Paquette, L. A., Ed.; Pergamon Press: Oxford, 1991; Vol. 5; Chapter 7.3.
3. (c) Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131.
4. (d) Grigg, R., Ed. Cascade Reactions. Tetrahedron Symposium in Print No. 62 1996, 52 (35).
5. (a) Denmark, S. E.; Thorarensen, A. Chem. Rev. (Washington, D.C.) 1996, 96, 137.
6. (b) Denmark, S. E.; Thorarensen, A.; Middleton, D. S. J. Am. Chem. Soc. 1996, 118, 8266.
7. (c) Denmark, S. E.; Thorarensen. A. J. Am. Chem. Soc. 1997, 119, 127.
8. (d) Denmark, S. E.; Hurd, A. R.; Sacha, H. J. J. Org. Chem. 1997, 62, 1668.
9. (e) Denmark, S. E.; Marcin, L. R. J. Org. Chem. 1997, 62, 1675.
10. (f) Denmark, S. E.; Guagnano, V.; Dixon, J. A.; Stolle, A. J. Org. Chem. 1997, 62, 4610.
11. (g) Denmark, S. E.; Dixon, J. A. J. Org. Chem. 1997, 62, 7086.
12. For preliminary reports see: (a) Denmark, S. E.; Senanayake, C. B. W.; Schnute, M. E.; Moon, Y. C.; Ho, G. D.; Middleton, D. S. Proceedings of the Fifth International Kyoto Conference on New Aspects of Organic Chemistry; VCH Verlagsgesellschaft and Kodansha Ltd.: Weinhein, 1992. (b) Denmark, S. E.; Schnute, M. E.; Thorarensen, A.; Middleton, D. S.; Stolle, A. Pure Appl. Chem. 1994, 66, 2041.
13. For preliminary reports see: (a) Denmark, S. E.; Senanayake, C. B. W.; Schnute, M. E.; Moon, Y. C.; Ho, G. D.; Middleton, D. S. Proceedings of the Fifth International Kyoto Conference on New Aspects of Organic Chemistry; VCH Verlagsgesellschaft and Kodansha Ltd.: Weinhein, 1992. (b) Denmark, S. E.; Schnute, M. E.; Thorarensen, A.; Middleton, D. S.; Stolle, A. Pure Appl. Chem. 1994, 66, 2041.
14. Seebach, D.; Knochel, P. Helv. Chim. Acta 1984, 67, 261.
15. Bachman, G. B.; Whitehouse, M. L. J. Org. Chem. 1967, 32, 2303.
16. Corey, E. J.; Estreicher, H. J. Am. Chem. Soc. 1978, 100, 6294.
17. Claus, R. E.; Schreiber, S. L. Org. Synth. 1985, 64, 150.
18. Hayama, T.; Tomoda, S.; Takeuchi, Y.; Nomura, Y. Chem. Lett. 1982, 1109 and references therein.
19. (a) Denmark, S. E.; Moon, Y. C.; Senanayake, C. B. W. J. Am. Chem. Soc. 1990, 112, 311 and references therein,
20. (b) Denmark, S. E.; Senanayake, C. B. W.; Ho, G. D. Tetrahedron 1990, 46, 4857.
21. (c) Denmark, S. E.; Senanayake, C. B. W. J. Org. Chem. 1993, 58, 1853.
22. (a) Denmark, S. E.; Schnute, M. E. J. Org. Chem. 1991, 56, 6738.
23. (b) Denmark, S. E.; Schnute, M. E.; Senanayake, C. B. W. J. Org. Chem. 1993, 58, 1859.
24. (c) Denmark, S. E.; Schnute, M. E.; Marcin, L. R.; Thorarensen, A. J. Org. Chem. 1995, 60, 3205.
25. (d) Denmark, S. E.; Thorarensen, A. J. Org. Chem. 1996, 61, 6727.
26. Schwartz, A.; Madan, P.; Whitesell, J. K.; Lawrence, R. M. Org. Synth. 1990, 69, 1.
27. (a) Pirkle, W. H.; Mahler, G.; Hyun, M. H. J. Liq. Chromatogr. 1986, 9, 443.
28. (b) Pirkle, W. H.; Pochapsky, T. C.; Burke, J. A.; Deming, K. C. In Chiral Separations; Stevenson, D., Wilson, I. D., Eds; Plenum: New York, 1988; p 23.
29. (c) Pirkle, W. H.; Pochapsky, T. C. Chem. Rev. 1989, 89, 347.
30. Trost, B. M.; Belletire, J. L.; Godleski, S.; McDougal, P. G.; Balkovec, J. M.; Baldwin, J. J.; Christy, M. E.; Ponticello, G. S.; Varga, S. L.; Springer, J. P. J Org. Chem. 1986, 51, 2370.
31. (a) Denmark, S. E.; Marcin, L. R. J. Org. Chem. 1993, 58, 3857.
32. (b) Denmark, S. E.; Schnute, M. E. J. Org. Chem. 1994, 59, 4576.
33. (c) Denmark, S. E.; Marcin, L. R. J. Org. Chem. 1995, 60, 3221.
34. Denmark, S. E.; Hurd, A. R. Manuscript submitted.
35. Denmark, S. E.; Kesler, B. S.; Moon, Y.-C. J. Org. Chem. 1992, 57, 4912.