Synthesis of norcarbovir analogues, the first examples of cyclobutene nucleosides unsubstituted at the vinylic position

Journal of Organic Chemistry

Volumn 62, Issue 7, 1997, Pages 2166-2172

  Gourdel Martin, Marie Edith ^a   Huet, François ^a  

^a UNIVERSITÉ DU MAINE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIVIRUS AGENT; CYCLOBUTANE DERIVATIVE; NUCLEOSIDE DERIVATIVE;

ANTIVIRAL ACTIVITY; ARTICLE; CELL STRAIN KB; CONTROLLED STUDY; CYTOTOXICITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS 2; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0030921946     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961451y     Document Type: Article

References (48)

1. For recent reviews, see the following, (a) Huryn, D. M.; Okabe, M. Chem. Rev. 1992, 92, 1745. (b) Borthwick, A. D.; Biggadike, K. Tetrahedron 1992, 48, 571. (c) Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S. R.; Earl, R. A.; Guedj, R. Tetrahedron 1994, 50, 10611.
2. For recent reviews, see the following, (a) Huryn, D. M.; Okabe, M. Chem. Rev. 1992, 92, 1745. (b) Borthwick, A. D.; Biggadike, K. Tetrahedron 1992, 48, 571. (c) Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S. R.; Earl, R. A.; Guedj, R. Tetrahedron 1994, 50, 10611.
3. For recent reviews, see the following, (a) Huryn, D. M.; Okabe, M. Chem. Rev. 1992, 92, 1745. (b) Borthwick, A. D.; Biggadike, K. Tetrahedron 1992, 48, 571. (c) Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S. R.; Earl, R. A.; Guedj, R. Tetrahedron 1994, 50, 10611.
4. Coates, J. A. V.; Inggall, H. J.; Pearson, B. A.; Penn, C. R.; Storer, R.; Williamson, C.; Cameron, J. M. Antiviral Res. 1991, 15, 161.
5. For recent syntheses, see the following, (a) Trost, B. M.; Li, L.; Guile, S. D. J. Am. Chem. Soc. 1992, 114, 8745. (b) Evans, C. T.; Roberts, S. M.; Shoberu, K. A.; Sutherland, A. G. J. Chem. Soc., Perkin Trans. 1 1992, 589. (c) Mac Keith, R. A.; Mc Cague, R.; Olivo, H. F.; Palmer, C. F.; Roberts, S. M. J. Chem. Soc., Perkin Trans. 1 1993, 313. (d) Jung, M. E.; Rhee, H. Tetrahedron Lett. 1993, 34, 449. (e) Asami, M.; Takahashi, J.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 1649. (f) Nokami, J.; Matsuura, H.; Nakasima, K.; Shibata, S. Chem. Lett. 1994, 1071. (g) Jung, M. E.; Rhee, H. J. Org. Chem. 1994, 59, 4719. (h) Diaz, M.; Ibarzo, J.; Jimenez, J. M.; Ortuno, R. M. Tetrahedron: Asymmetry 1994, 5, 129. (i) Legraverend, M.; Aubertin, A. M.; Obert G.; Huel, C.; Bisagni, E. Nucleosides Nudeotides 1994, 13, 915. (j) Hildebrand, S.; Troxler, T.; Scheffold, R. Helv. Chim. Acta 1994, 77, 1236. (k) Berranger, T.; Langlois, Y. Tetrahedron Lett. 1995, 36, 5523. (1) Crimmins, M. T.; King, B. W. J. Org. Chem. 1996, 61, 4192. See also references therein.
6. For recent syntheses, see the following, (a) Trost, B. M.; Li, L.; Guile, S. D. J. Am. Chem. Soc. 1992, 114, 8745. (b) Evans, C. T.; Roberts, S. M.; Shoberu, K. A.; Sutherland, A. G. J. Chem. Soc., Perkin Trans. 1 1992, 589. (c) Mac Keith, R. A.; Mc Cague, R.; Olivo, H. F.; Palmer, C. F.; Roberts, S. M. J. Chem. Soc., Perkin Trans. 1 1993, 313. (d) Jung, M. E.; Rhee, H. Tetrahedron Lett. 1993, 34, 449. (e) Asami, M.; Takahashi, J.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 1649. (f) Nokami, J.; Matsuura, H.; Nakasima, K.; Shibata, S. Chem. Lett. 1994, 1071. (g) Jung, M. E.; Rhee, H. J. Org. Chem. 1994, 59, 4719. (h) Diaz, M.; Ibarzo, J.; Jimenez, J. M.; Ortuno, R. M. Tetrahedron: Asymmetry 1994, 5, 129. (i) Legraverend, M.; Aubertin, A. M.; Obert G.; Huel, C.; Bisagni, E. Nucleosides Nudeotides 1994, 13, 915. (j) Hildebrand, S.; Troxler, T.; Scheffold, R. Helv. Chim. Acta 1994, 77, 1236. (k) Berranger, T.; Langlois, Y. Tetrahedron Lett. 1995, 36, 5523. (1) Crimmins, M. T.; King, B. W. J. Org. Chem. 1996, 61, 4192. See also references therein.
7. For recent syntheses, see the following, (a) Trost, B. M.; Li, L.; Guile, S. D. J. Am. Chem. Soc. 1992, 114, 8745. (b) Evans, C. T.; Roberts, S. M.; Shoberu, K. A.; Sutherland, A. G. J. Chem. Soc., Perkin Trans. 1 1992, 589. (c) Mac Keith, R. A.; Mc Cague, R.; Olivo, H. F.; Palmer, C. F.; Roberts, S. M. J. Chem. Soc., Perkin Trans. 1 1993, 313. (d) Jung, M. E.; Rhee, H. Tetrahedron Lett. 1993, 34, 449. (e) Asami, M.; Takahashi, J.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 1649. (f) Nokami, J.; Matsuura, H.; Nakasima, K.; Shibata, S. Chem. Lett. 1994, 1071. (g) Jung, M. E.; Rhee, H. J. Org. Chem. 1994, 59, 4719. (h) Diaz, M.; Ibarzo, J.; Jimenez, J. M.; Ortuno, R. M. Tetrahedron: Asymmetry 1994, 5, 129. (i) Legraverend, M.; Aubertin, A. M.; Obert G.; Huel, C.; Bisagni, E. Nucleosides Nudeotides 1994, 13, 915. (j) Hildebrand, S.; Troxler, T.; Scheffold, R. Helv. Chim. Acta 1994, 77, 1236. (k) Berranger, T.; Langlois, Y. Tetrahedron Lett. 1995, 36, 5523. (1) Crimmins, M. T.; King, B. W. J. Org. Chem. 1996, 61, 4192. See also references therein.
8. For recent syntheses, see the following, (a) Trost, B. M.; Li, L.; Guile, S. D. J. Am. Chem. Soc. 1992, 114, 8745. (b) Evans, C. T.; Roberts, S. M.; Shoberu, K. A.; Sutherland, A. G. J. Chem. Soc., Perkin Trans. 1 1992, 589. (c) Mac Keith, R. A.; Mc Cague, R.; Olivo, H. F.; Palmer, C. F.; Roberts, S. M. J. Chem. Soc., Perkin Trans. 1 1993, 313. (d) Jung, M. E.; Rhee, H. Tetrahedron Lett. 1993, 34, 449. (e) Asami, M.; Takahashi, J.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 1649. (f) Nokami, J.; Matsuura, H.; Nakasima, K.; Shibata, S. Chem. Lett. 1994, 1071. (g) Jung, M. E.; Rhee, H. J. Org. Chem. 1994, 59, 4719. (h) Diaz, M.; Ibarzo, J.; Jimenez, J. M.; Ortuno, R. M. Tetrahedron: Asymmetry 1994, 5, 129. (i) Legraverend, M.; Aubertin, A. M.; Obert G.; Huel, C.; Bisagni, E. Nucleosides Nudeotides 1994, 13, 915. (j) Hildebrand, S.; Troxler, T.; Scheffold, R. Helv. Chim. Acta 1994, 77, 1236. (k) Berranger, T.; Langlois, Y. Tetrahedron Lett. 1995, 36, 5523. (1) Crimmins, M. T.; King, B. W. J. Org. Chem. 1996, 61, 4192. See also references therein.
9. For recent syntheses, see the following, (a) Trost, B. M.; Li, L.; Guile, S. D. J. Am. Chem. Soc. 1992, 114, 8745. (b) Evans, C. T.; Roberts, S. M.; Shoberu, K. A.; Sutherland, A. G. J. Chem. Soc., Perkin Trans. 1 1992, 589. (c) Mac Keith, R. A.; Mc Cague, R.; Olivo, H. F.; Palmer, C. F.; Roberts, S. M. J. Chem. Soc., Perkin Trans. 1 1993, 313. (d) Jung, M. E.; Rhee, H. Tetrahedron Lett. 1993, 34, 449. (e) Asami, M.; Takahashi, J.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 1649. (f) Nokami, J.; Matsuura, H.; Nakasima, K.; Shibata, S. Chem. Lett. 1994, 1071. (g) Jung, M. E.; Rhee, H. J. Org. Chem. 1994, 59, 4719. (h) Diaz, M.; Ibarzo, J.; Jimenez, J. M.; Ortuno, R. M. Tetrahedron: Asymmetry 1994, 5, 129. (i) Legraverend, M.; Aubertin, A. M.; Obert G.; Huel, C.; Bisagni, E. Nucleosides Nudeotides 1994, 13, 915. (j) Hildebrand, S.; Troxler, T.; Scheffold, R. Helv. Chim. Acta 1994, 77, 1236. (k) Berranger, T.; Langlois, Y. Tetrahedron Lett. 1995, 36, 5523. (1) Crimmins, M. T.; King, B. W. J. Org. Chem. 1996, 61, 4192. See also references therein.
10. For recent syntheses, see the following, (a) Trost, B. M.; Li, L.; Guile, S. D. J. Am. Chem. Soc. 1992, 114, 8745. (b) Evans, C. T.; Roberts, S. M.; Shoberu, K. A.; Sutherland, A. G. J. Chem. Soc., Perkin Trans. 1 1992, 589. (c) Mac Keith, R. A.; Mc Cague, R.; Olivo, H. F.; Palmer, C. F.; Roberts, S. M. J. Chem. Soc., Perkin Trans. 1 1993, 313. (d) Jung, M. E.; Rhee, H. Tetrahedron Lett. 1993, 34, 449. (e) Asami, M.; Takahashi, J.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 1649. (f) Nokami, J.; Matsuura, H.; Nakasima, K.; Shibata, S. Chem. Lett. 1994, 1071. (g) Jung, M. E.; Rhee, H. J. Org. Chem. 1994, 59, 4719. (h) Diaz, M.; Ibarzo, J.; Jimenez, J. M.; Ortuno, R. M. Tetrahedron: Asymmetry 1994, 5, 129. (i) Legraverend, M.; Aubertin, A. M.; Obert G.; Huel, C.; Bisagni, E. Nucleosides Nudeotides 1994, 13, 915. (j) Hildebrand, S.; Troxler, T.; Scheffold, R. Helv. Chim. Acta 1994, 77, 1236. (k) Berranger, T.; Langlois, Y. Tetrahedron Lett. 1995, 36, 5523. (1) Crimmins, M. T.; King, B. W. J. Org. Chem. 1996, 61, 4192. See also references therein.
11. For recent syntheses, see the following, (a) Trost, B. M.; Li, L.; Guile, S. D. J. Am. Chem. Soc. 1992, 114, 8745. (b) Evans, C. T.; Roberts, S. M.; Shoberu, K. A.; Sutherland, A. G. J. Chem. Soc., Perkin Trans. 1 1992, 589. (c) Mac Keith, R. A.; Mc Cague, R.; Olivo, H. F.; Palmer, C. F.; Roberts, S. M. J. Chem. Soc., Perkin Trans. 1 1993, 313. (d) Jung, M. E.; Rhee, H. Tetrahedron Lett. 1993, 34, 449. (e) Asami, M.; Takahashi, J.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 1649. (f) Nokami, J.; Matsuura, H.; Nakasima, K.; Shibata, S. Chem. Lett. 1994, 1071. (g) Jung, M. E.; Rhee, H. J. Org. Chem. 1994, 59, 4719. (h) Diaz, M.; Ibarzo, J.; Jimenez, J. M.; Ortuno, R. M. Tetrahedron: Asymmetry 1994, 5, 129. (i) Legraverend, M.; Aubertin, A. M.; Obert G.; Huel, C.; Bisagni, E. Nucleosides Nudeotides 1994, 13, 915. (j) Hildebrand, S.; Troxler, T.; Scheffold, R. Helv. Chim. Acta 1994, 77, 1236. (k) Berranger, T.; Langlois, Y. Tetrahedron Lett. 1995, 36, 5523. (1) Crimmins, M. T.; King, B. W. J. Org. Chem. 1996, 61, 4192. See also references therein.
12. For recent syntheses, see the following, (a) Trost, B. M.; Li, L.; Guile, S. D. J. Am. Chem. Soc. 1992, 114, 8745. (b) Evans, C. T.; Roberts, S. M.; Shoberu, K. A.; Sutherland, A. G. J. Chem. Soc., Perkin Trans. 1 1992, 589. (c) Mac Keith, R. A.; Mc Cague, R.; Olivo, H. F.; Palmer, C. F.; Roberts, S. M. J. Chem. Soc., Perkin Trans. 1 1993, 313. (d) Jung, M. E.; Rhee, H. Tetrahedron Lett. 1993, 34, 449. (e) Asami, M.; Takahashi, J.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 1649. (f) Nokami, J.; Matsuura, H.; Nakasima, K.; Shibata, S. Chem. Lett. 1994, 1071. (g) Jung, M. E.; Rhee, H. J. Org. Chem. 1994, 59, 4719. (h) Diaz, M.; Ibarzo, J.; Jimenez, J. M.; Ortuno, R. M. Tetrahedron: Asymmetry 1994, 5, 129. (i) Legraverend, M.; Aubertin, A. M.; Obert G.; Huel, C.; Bisagni, E. Nucleosides Nudeotides 1994, 13, 915. (j) Hildebrand, S.; Troxler, T.; Scheffold, R. Helv. Chim. Acta 1994, 77, 1236. (k) Berranger, T.; Langlois, Y. Tetrahedron Lett. 1995, 36, 5523. (1) Crimmins, M. T.; King, B. W. J. Org. Chem. 1996, 61, 4192. See also references therein.
13. For recent syntheses, see the following, (a) Trost, B. M.; Li, L.; Guile, S. D. J. Am. Chem. Soc. 1992, 114, 8745. (b) Evans, C. T.; Roberts, S. M.; Shoberu, K. A.; Sutherland, A. G. J. Chem. Soc., Perkin Trans. 1 1992, 589. (c) Mac Keith, R. A.; Mc Cague, R.; Olivo, H. F.; Palmer, C. F.; Roberts, S. M. J. Chem. Soc., Perkin Trans. 1 1993, 313. (d) Jung, M. E.; Rhee, H. Tetrahedron Lett. 1993, 34, 449. (e) Asami, M.; Takahashi, J.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 1649. (f) Nokami, J.; Matsuura, H.; Nakasima, K.; Shibata, S. Chem. Lett. 1994, 1071. (g) Jung, M. E.; Rhee, H. J. Org. Chem. 1994, 59, 4719. (h) Diaz, M.; Ibarzo, J.; Jimenez, J. M.; Ortuno, R. M. Tetrahedron: Asymmetry 1994, 5, 129. (i) Legraverend, M.; Aubertin, A. M.; Obert G.; Huel, C.; Bisagni, E. Nucleosides Nudeotides 1994, 13, 915. (j) Hildebrand, S.; Troxler, T.; Scheffold, R. Helv. Chim. Acta 1994, 77, 1236. (k) Berranger, T.; Langlois, Y. Tetrahedron Lett. 1995, 36, 5523. (1) Crimmins, M. T.; King, B. W. J. Org. Chem. 1996, 61, 4192. See also references therein.
14. For recent syntheses, see the following, (a) Trost, B. M.; Li, L.; Guile, S. D. J. Am. Chem. Soc. 1992, 114, 8745. (b) Evans, C. T.; Roberts, S. M.; Shoberu, K. A.; Sutherland, A. G. J. Chem. Soc., Perkin Trans. 1 1992, 589. (c) Mac Keith, R. A.; Mc Cague, R.; Olivo, H. F.; Palmer, C. F.; Roberts, S. M. J. Chem. Soc., Perkin Trans. 1 1993, 313. (d) Jung, M. E.; Rhee, H. Tetrahedron Lett. 1993, 34, 449. (e) Asami, M.; Takahashi, J.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 1649. (f) Nokami, J.; Matsuura, H.; Nakasima, K.; Shibata, S. Chem. Lett. 1994, 1071. (g) Jung, M. E.; Rhee, H. J. Org. Chem. 1994, 59, 4719. (h) Diaz, M.; Ibarzo, J.; Jimenez, J. M.; Ortuno, R. M. Tetrahedron: Asymmetry 1994, 5, 129. (i) Legraverend, M.; Aubertin, A. M.; Obert G.; Huel, C.; Bisagni, E. Nucleosides Nudeotides 1994, 13, 915. (j) Hildebrand, S.; Troxler, T.; Scheffold, R. Helv. Chim. Acta 1994, 77, 1236. (k) Berranger, T.; Langlois, Y. Tetrahedron Lett. 1995, 36, 5523. (1) Crimmins, M. T.; King, B. W. J. Org. Chem. 1996, 61, 4192. See also references therein.
15. For recent syntheses, see the following, (a) Trost, B. M.; Li, L.; Guile, S. D. J. Am. Chem. Soc. 1992, 114, 8745. (b) Evans, C. T.; Roberts, S. M.; Shoberu, K. A.; Sutherland, A. G. J. Chem. Soc., Perkin Trans. 1 1992, 589. (c) Mac Keith, R. A.; Mc Cague, R.; Olivo, H. F.; Palmer, C. F.; Roberts, S. M. J. Chem. Soc., Perkin Trans. 1 1993, 313. (d) Jung, M. E.; Rhee, H. Tetrahedron Lett. 1993, 34, 449. (e) Asami, M.; Takahashi, J.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 1649. (f) Nokami, J.; Matsuura, H.; Nakasima, K.; Shibata, S. Chem. Lett. 1994, 1071. (g) Jung, M. E.; Rhee, H. J. Org. Chem. 1994, 59, 4719. (h) Diaz, M.; Ibarzo, J.; Jimenez, J. M.; Ortuno, R. M. Tetrahedron: Asymmetry 1994, 5, 129. (i) Legraverend, M.; Aubertin, A. M.; Obert G.; Huel, C.; Bisagni, E. Nucleosides Nudeotides 1994, 13, 915. (j) Hildebrand, S.; Troxler, T.; Scheffold, R. Helv. Chim. Acta 1994, 77, 1236. (k) Berranger, T.; Langlois, Y. Tetrahedron Lett. 1995, 36, 5523. (1) Crimmins, M. T.; King, B. W. J. Org. Chem. 1996, 61, 4192. See also references therein.
16. For recent syntheses, see the following, (a) Trost, B. M.; Li, L.; Guile, S. D. J. Am. Chem. Soc. 1992, 114, 8745. (b) Evans, C. T.; Roberts, S. M.; Shoberu, K. A.; Sutherland, A. G. J. Chem. Soc., Perkin Trans. 1 1992, 589. (c) Mac Keith, R. A.; Mc Cague, R.; Olivo, H. F.; Palmer, C. F.; Roberts, S. M. J. Chem. Soc., Perkin Trans. 1 1993, 313. (d) Jung, M. E.; Rhee, H. Tetrahedron Lett. 1993, 34, 449. (e) Asami, M.; Takahashi, J.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 1649. (f) Nokami, J.; Matsuura, H.; Nakasima, K.; Shibata, S. Chem. Lett. 1994, 1071. (g) Jung, M. E.; Rhee, H. J. Org. Chem. 1994, 59, 4719. (h) Diaz, M.; Ibarzo, J.; Jimenez, J. M.; Ortuno, R. M. Tetrahedron: Asymmetry 1994, 5, 129. (i) Legraverend, M.; Aubertin, A. M.; Obert G.; Huel, C.; Bisagni, E. Nucleosides Nudeotides 1994, 13, 915. (j) Hildebrand, S.; Troxler, T.; Scheffold, R. Helv. Chim. Acta 1994, 77, 1236. (k) Berranger, T.; Langlois, Y. Tetrahedron Lett. 1995, 36, 5523. (1) Crimmins, M. T.; King, B. W. J. Org. Chem. 1996, 61, 4192. See also references therein.
17. Binns, F.; Hayes, R.; Hodgetts, K. J.; Saengchantara, S. T.; Wallace, T. W.; Wallis, C. J. Tetrahedron 1996, 42, 3631.
18. (a) Trost, B. M.; McDougal, P. G. J. Org. Chem. 1984, 49, 458.
19. (b) Tamm, C.; Jeker, N. Tetrahedron 1989, 45, 2385.
20. (c) Vos, G. J. M.; Benders, P. H.; Reinhoudt, D. N.; Egberink, R. J. M.; Harkema, S.; van Hummel, G. J. J. Org. Chem. 1986, 51, 2004.
21. (a) Maruyama, T.; Hanai, Y.; Sato, Y. Nucleosides Nucleotides 1992, 11, 855.
22. (b) Maruyama, T.; Hanai, Y.; Sato, Y.; Snoeck, R.; Andrei, G.; Hosoya, M.; Balzarini, J.; De Clercq, E. Chem. Pharm. Bull. 1993, 41, 516.
23. Gharbaoui, T.; Legraverend, M.; Bisagni, E. Tetrahedron Lett. 1992, 33, 7141.
24. (a) Bloomfield, J. J.; Owsley, D. C. Org. Photochem. Synth. 1976, 2, 36.
25. (b) Binns, F.; Hayes, R.; Ingham, S.; Saengchantara, S. T.; Turner, R. W.; Wallace, T. W. Tetrahedron 1992, 48, 515.
26. (c) Brauman, J. I.; Archie, W. C., Jr. J. Am. Chem. Soc. 1972, 94, 4262.
27. (a) Soai, K.; Yokoyama, S.; Mochida, K. Synthesis 1987, 647.
28. (b) Mévellec, L.; Evers, M.; Huet, F. Tetrahedron 1996, 48, 15103.
29. Moriarty, R. M.; Chany, C. J., II; Void, R. K.; Prakash, O.; Tuladhar, S. M. J. Org. Chem. 1993, 58, 2478.
30. Gourdel-Martin, M.-E.; Huet, F. Tetrahedron Lett. 1996, 37, 7745 and references therein.
31. (a) Ishizuka, T.; Kunieda, T. Tetrahedron Lett. 1987, 28, 4185.
32. (b) Taylor, S. J. C.; Me Cague, R.; Wisdom, R.; Lee, C.; Dickson, K.; Ruecroft, G.; O'Brien, F.; Littlechild, J.; Bevan, J.; Roberts, S. M.; Evans, C. T. Tetrahedron: Asymmetry 1993, 4, 1117.
33. (a) Marquez, V. E.; Lim, B. B.; Driscoll, J. S.; Snoek, R.; Balzarini, J.; Ikeda, S.; Andrei, G.; De Clercq, E. J. Heterocycl. Chem. 1993, 30, 1393.
34. (b) Agrofoglio, L.; Condom, R.; Guedj, R.; Challand, R.; Selway, J. Tetrahedron Lett. 1993, 34, 6271.
35. (c) Payne, A. N.; Roberts, S. M. J. Chem. Soc., Perkin Trans. 1 1992, 2633.
36. (d) Coe, D. M.; Myers, P. L.; Parry, D. M.; Roberts, S. M.; Storer, R. J. Chem. Soc., Chem. Commun. 1990, 151.
37. (e) Palmer, C. F.; Parry, K. P.; Roberts, S. M. Tetrahedron Lett. 1990, 31, 279.
38. (a) Louis-Andre, O.; Gelbard, G. Bull. Soc. Chim. Fr. 1986, 565.
39. (b) O'Hara Dempcy, R.; Skibo, E. B. J. Org. Chem. 1991, 56, 776.
40. For a similar observation, see: Boothroyd, S. R.; Kerr, M. A. Tetrahedron Lett. 1995, 36, 2411.
41. Petrini, M.; Ballini, R.; Rosini, G. Synthesis 1987, 713.
42. Entwistle, I. D.; Johnstone, R. A. W.; Telford, R. P. J. Chem. Soc., Perkin Trans. 1 1977, 443.
43. (a) Baik, W.; Han, J. L.; Lee, K. C.; Lee, N. H.; Kim, B. H.; Hahn, J.-T. Tetrahedron Lett. 1994, 35, 3965.
44. (b) Davey, C. L.; Powell, L. W.; Turner, N. J.; Wells, A. Tetrahedron Lett. 1994, 35, 7867.
45. Bellamy, F. D.; Ou, K. Tetrahedron Lett. 1984, 25, 839.
46. Durst, T.; Breau, L. Cyclobutene Ring Opening Reactions. In Comprehensive Organic Synthesis; Trost, B. M., Flemming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, Chapter 6.1 pp 665- 697.
47. (a) Binns, F.; Hayes, R.; Ingham, S.; Saengchantara, S. T.; Turner, R. W.; Wallace, T. W. Tetrahedron 1992, 48, 515.
48. (b) Houk, K. N.; Li, Y.; Evanseck, J. D. Angew. Chem., Int. Ed. Engl. 1992, 31, 682.