Heterocyclic routes to polysubstituted cyclopentanes: Molecular modelling of electrophilic additions to di- and trisubstituted cyclopentenes

Tetrahedron

Volumn 52, Issue 9, 1996, Pages 3355-3364

  Nichols, Jason ^a   Tralka, Tara ^a   Goering, Bradley K ^a   Wilcox, Charles F ^a   Ganem, Bruce ^a  

^a Department of Population Medicine and Diagnostic Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030056356     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)01116-1     Document Type: Article

References (53)

1. (a) Lasky, L. A. Science 1992, 258, 964;
2. (b) Feizi, T. TIBS 1991, 16, 84;
3. (c) Springer, T. Nature 1990, 346, 425.
4. Cohen, P.; Houslay, M. D.; Eds., Molecular Mechanism of Transmembrane Signalling (Elsevier, Amsterdam, 1985).
5. Winchester, B.; Fleet, G. W. J. Glycobiology 1992, 2, 199
6. (a) Aoyagi, T.; Yamamoto, T.; Kojiri, K.; Morishima, H.; Nagai, M.; Hamada, M.; Takeuchi, T.; Umezawa, H. J. Antibiot. 1989, 42, 883;
7. (b) Morishima, H.; Kojiri, K.; Yamamoto, T.; Aoyagi, T.; Nakamura, H.; Iitaka, Y. J. Antibiot. 1989, 42, 1008.
8. (a) Sakuda, S.; Isogai, A.; Matsumoto, S.; Suzuki, A.; Koseki, K.; Kodama, H.; Suzuki, A. Agric. Biol. Chem. 1987, 51, 3251;
9. (b) Sakuda, S.; Isogai, A.; Makita, T.; Matsumoto, S.; Suzuki, A.; Koseki, K.; Kodama, H.; Yamada, Y. Agric. Biol. Chem. 1988, 52, 1615.
10. Uchida, C.; Yamagishi, T.; Ogawa, S. J. Chem. Soc. Perkin 1 1994, 589.
11. (a) Knapp, S.; Murali Dhar, T. G. J. Org. Chem. 1991, 56, 4096;
12. (b) Knapp, S.; Purandare, A.; Rupitz, K.; Withers, S. G. J. Am. Chem. Soc. 1994, 116, 7461.
13. Nakata, M.; Akazawa, S.; Kitamura, S.; Tatsuka, K. Tetrahedron Lett. 1991, 32, 5363.
14. (a) Simpkins, N. S.; Stokes, S; Whittle, A. J. Tetrahedron Lett. 1992, 33, 793;
15. (b) idem, J. Chem. Soc. Perkin Trans. 1 1992, 2471.
16. Kobayashi, Y.; Miyazaki, H.; Shiozaki, M. J. Org. Chem. 1994, 59, 813.
17. Uchida, C.; Yamagishi, T.; Ogawa, J. J. Chem. Soc. Perkin Trans. 1 1994, 589.
18. Li, C.; Fuchs, P. L. Tetrahedron Lett. 1994, 35, 5121.
19. Kiguchi, T.; Tajiri, K.; Minomiya, L.; Naito, T.; Hiramatsu, H. Tetrahedron Lett. 1995, 36, 253.
20. (a) Takahashi, S.; Terayama, H.; Kuzuhara, H. Tetrahedron Lett. 1991, 32, 5123;
21. (b) Takahashi, S.; Terayama, H.; Kuzuhara, H. Tetrahedron Lett. 1992, 33, 7565;
22. (c) Takahashi, S.; Inoue, H.; Kuzuhara, H. J. Carb. Chem. 1995, 14, 273.
23. Griffith, D. A.; Danishefsky, S. J. J. Am. Chem. Soc. 1991, 113, 5863.
24. (a) Trost, B. M.; van Vranken, D. L. J. Am. Chem. Soc. 1990, 112, 1261;
25. (b) idem J. Am. Chem. Soc. 1991, 113, 6317;
26. (b) idem J. Am. Chem. Soc. 1993, 115, 444.
27. (a) Maloisel, J.-L.; Vasella, A,; Trost, B. M.; van Vranken, D. L. J. Chem. Soc. Chem. Commun. 1991, 1099;
28. (b) idem, Helv. Chim. Acta 1992, 75, 1515.
29. (a) King, S. B.; Ganem, B. J. Am. Chem. Soc. 1991, 113, 5089;
30. (b) King, S. B.; Ganem, B. J. Am. Chem. Soc. 1994, 116, 562.
31. Goering, B. K.; Ganem, B. Tetrahedron Lett. 1994, 35, 6997.
32. Goering, B. K.; Li, J.; Ganem, B. Tetrahedron Lett. 1995, 36, 0000.
33. See for example: (a) Poli, G.; Tetrahedron Lett. 1989, 30, 7385;
34. (b) Johnson, C. R.; Penning, T. D. J. Am. Chem. Soc. 1988, 110, 4726.
35. Goering, B. K. Ph.D. Thesis, Cornell University, Ithaca, NY; 1995.
36. Roberts, I.; Kimball, G. E. J. Am. Chem. Soc. 1937, 59, 947.
37. Fahey, R. C. Top. Stereochem. 1968, 3, 237.
38. Olah, G. "Halonium Ions," Wiley-Interscience, New York, 1975.
39. (a) Slebocka-Tilk, H.; Ball, R. G.; Brown, R. S. J. Am. Chem. Soc. 1985, 107, 4504.
40. Brown, R. S.; Nagorski, R. W.; Bennet, A. J.; McClung, R. E. D.; Aarts, G. H. M.; Klobukowski, M.; McDonald, R.; Santarsiero, B. D. J. Am. Chem. Soc. 1994, 116, 2448.
41. (a) Stewart, J. J. P. J. Comput. Chem. 1989, 10, 209;
42. (b) idem, ibid. 221.
43. Stewart, J. J. P. QCPE #504, Quantum Chemical Program Exchange, Indiana University, Bloomington, IN 47405.
44. Serena Software, Box 3076, Bloomington, IN 47402-3076.
45. (a) Winstein, S.; Lucas, H. J. J. Am. Chem. Soc. 1939, 61, 1576; 2845;
46. (b) Winstein, S.; Ingrahm, L. L. J. Am. Chem. Soc. 1952, 74, 1160.
47. (a) Poirier, R. A.; Mezey, P. G.; Yates, K.; Csizmadia, I. G. J. Mol. Struct. (THEOCHEM) 1981, 85, 153;
48. (b) Poirier, R. A.; DeMaré, G. R.; Yates, K.; Csizmadia, I. G. J. Mol. Struct. (THEOCHEM) 1983, 94, 137.
49. Hamilton, T. P.; Schaefer, H. F., III J. Am. Chem. Soc. 1990, 112, 8260.
50. Slebocka-Tilk, H.; Motallebi, S.; Nagorski, R. W.; Turner, P.; Brown, R. S.; McDonald, R. J. Am. Chem. Soc. 1995, 117, 8769.
51. Beppu, Y. QCPE #370, Quantum Chemical Program Exchange, Indiana University, Bloomington, IN 47405.
52. Onsager, L. J. Am. Chem. Soc. 1938, 58, 1486.
53. Wiberg, K. B. "Physical Organic Chemistry," Wiley, New York, 1964, p. 381.