The first α-fluoroallenylphosphonate, the synthesis of conjugated fluoroenynes, and the stereoselective synthesis of vinylfluorophosphonates using a new multifunctional fluorine-containing building block

Journal of Organic Chemistry

Volumn 65, Issue 1, 2000, Pages 227-234

  Zapata, Antonio J ^a,b   Gu, Yonghong ^a   Hammond, Gerald B ^a  

^a UNIVERSITY OF MASSACHUSETTS DARTMOUTH   (United States)

^b UNIVERSIDAD SIMÓN BOLÍVAR   (Venezuela)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL DERIVATIVE; FLUORINE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033966640     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991620p     Document Type: Article

References (102)

1. Hudlicky, M.; Pavlath, A. E. Chemistry of Organic Fluorine Compounds II; American Chemical Society: Washington, DC, 1995. Biomedical Frontiers of Fluorine Chemistry; Ojima, I., McCarthy, J. R., Welch, J. T., Eds.; American Chemical Society: Washington, DC, 1996; Vol. 639. Welch, J. T.; Eswarakrishnan, S. Fluorine in Bioorganic Chemistry; Wiley-Interscience: New York, 1991.
2. Hudlicky, M.; Pavlath, A. E. Chemistry of Organic Fluorine Compounds II; American Chemical Society: Washington, DC, 1995. Biomedical Frontiers of Fluorine Chemistry; Ojima, I., McCarthy, J. R., Welch, J. T., Eds.; American Chemical Society: Washington, DC, 1996; Vol. 639. Welch, J. T.; Eswarakrishnan, S. Fluorine in Bioorganic Chemistry; Wiley-Interscience: New York, 1991.
3. Hudlicky, M.; Pavlath, A. E. Chemistry of Organic Fluorine Compounds II; American Chemical Society: Washington, DC, 1995. Biomedical Frontiers of Fluorine Chemistry; Ojima, I., McCarthy, J. R., Welch, J. T., Eds.; American Chemical Society: Washington, DC, 1996; Vol. 639. Welch, J. T.; Eswarakrishnan, S. Fluorine in Bioorganic Chemistry; Wiley-Interscience: New York, 1991.
4. Schlosser, M. Angew. Chem., Int. Ed. Engl. 1998, 110, 1496-1513. Johnson, W. S.; Chenera, B.; Tham, F. S.; Kullnig, R. K. J. Am. Chem. Soc. 1993, 115, 493-497. Moran, S.; Ren, R. X.-F.; Rumney, S., IV; Kool, E. T. J. Am. Chem. Soc. 1997, 119, 2056-2057. Evans, T. A.; Seddon, K. R. J. Chem. Soc., Chem. Commun. 1997, 2023-2024.
5. Schlosser, M. Angew. Chem., Int. Ed. Engl. 1998, 110, 1496- 1513. Johnson, W. S.; Chenera, B.; Tham, F. S.; Kullnig, R. K. J. Am. Chem. Soc. 1993, 115, 493-497. Moran, S.; Ren, R. X.-F.; Rumney, S., IV; Kool, E. T. J. Am. Chem. Soc. 1997, 119, 2056-2057. Evans, T. A.; Seddon, K. R. J. Chem. Soc., Chem. Commun. 1997, 2023-2024.
6. Schlosser, M. Angew. Chem., Int. Ed. Engl. 1998, 110, 1496- 1513. Johnson, W. S.; Chenera, B.; Tham, F. S.; Kullnig, R. K. J. Am. Chem. Soc. 1993, 115, 493-497. Moran, S.; Ren, R. X.-F.; Rumney, S., IV; Kool, E. T. J. Am. Chem. Soc. 1997, 119, 2056-2057. Evans, T. A.; Seddon, K. R. J. Chem. Soc., Chem. Commun. 1997, 2023-2024.
7. Schlosser, M. Angew. Chem., Int. Ed. Engl. 1998, 110, 1496- 1513. Johnson, W. S.; Chenera, B.; Tham, F. S.; Kullnig, R. K. J. Am. Chem. Soc. 1993, 115, 493-497. Moran, S.; Ren, R. X.-F.; Rumney, S., IV; Kool, E. T. J. Am. Chem. Soc. 1997, 119, 2056-2057. Evans, T. A.; Seddon, K. R. J. Chem. Soc., Chem. Commun. 1997, 2023-2024.
8. (a) Organo-Fluorine Compounds; Baasner, B., Hagemann, H., Tatlow, J. C., Eds.; Thieme: Stuttgart, 1999; Vol. E10a, Fluorinating Agents.
9. (b) Other reviews include: Tozer, M. J.; Herpin, T. F. Tetrahedron 1996, 52, 8619-8683. Wilkinson, J. A. Chem. Rev. 1992, 92, 505-519. New reagents used in nucleophilic fluorination: Pilcher, A. S.; Ammon, H. L.; DeShong, P. J. Am. Chem. Soc. 1995, 117, 5166- 5167. Hagiwara, T.; Fuchikami, T. Synlett 1995, 717-718.
10. (b) Other reviews include: Tozer, M. J.; Herpin, T. F. Tetrahedron 1996, 52, 8619-8683. Wilkinson, J. A. Chem. Rev. 1992, 92, 505-519. New reagents used in nucleophilic fluorination: Pilcher, A. S.; Ammon, H. L.; DeShong, P. J. Am. Chem. Soc. 1995, 117, 5166- 5167. Hagiwara, T.; Fuchikami, T. Synlett 1995, 717-718.
11. (b) Other reviews include: Tozer, M. J.; Herpin, T. F. Tetrahedron 1996, 52, 8619-8683. Wilkinson, J. A. Chem. Rev. 1992, 92, 505-519. New reagents used in nucleophilic fluorination: Pilcher, A. S.; Ammon, H. L.; DeShong, P. J. Am. Chem. Soc. 1995, 117, 5166-5167. Hagiwara, T.; Fuchikami, T. Synlett 1995, 717-718.
12. (b) Other reviews include: Tozer, M. J.; Herpin, T. F. Tetrahedron 1996, 52, 8619-8683. Wilkinson, J. A. Chem. Rev. 1992, 92, 505-519. New reagents used in nucleophilic fluorination: Pilcher, A. S.; Ammon, H. L.; DeShong, P. J. Am. Chem. Soc. 1995, 117, 5166- 5167. Hagiwara, T.; Fuchikami, T. Synlett 1995, 717-718.
13. For an updated compilation of references, see: Percy, J. M. Top. Curr. Chem. 1997, 193, 131-195.
14. For recent background information see: O'Hagan, D.; Rzepa, H. S. J. Chem. Soc., Chem. Commun. 1997, 645-652.
15. Perfluorinated phosphonates have been synthesized via photochemical and thermal reactions. See: Nair, H.; Burton, D. J. J. Am. Chem. Soc. 1997, 119, 9137-9143. For a recent review of fluorinated ylides see: Burton, D. J., Yang, Z.-Y., Qiu, W. Chem. Rev. 1996, 96, 1641-1716.
16. Perfluorinated phosphonates have been synthesized via photochemical and thermal reactions. See: Nair, H.; Burton, D. J. J. Am. Chem. Soc. 1997, 119, 9137-9143. For a recent review of fluorinated ylides see: Burton, D. J., Yang, Z.-Y., Qiu, W. Chem. Rev. 1996, 96, 1641-1716.
17. Blackburn, G. M.; Parratt, M. J. J. Chem. Soc., Perkin Trans. 1 1986, 1417-24. Blackburn, G. M.; Kent, D. E. J. Chem. Soc., Perkin Trans. 1 1986, 913-917. Blackburn, G. M.; Brown, D.; Martin, S. J.; Parratt, M. J. J. Chem. Soc., Perkin Trans. 1 1987, 181-186. Waschbusch, R.; Carran, J.; Savignac, P. J. Chem. Soc., Perkin Trans. 1 1997, 1135-1139. Waschbusch, R.; Carran, J.; Savignac, P. Tetrahedron 1997, 53, 6391-6400. Patois, C.; Savignac, P. J. Chem. Soc., Chem. Commun. 1993, 1711-1712. Differding, E.; Duthaler, R. O.; Krieger, A.; Rueegg, G. M.; Schmit, C. Synlett 1991, 395-396.
18. Blackburn, G. M.; Parratt, M. J. J. Chem. Soc., Perkin Trans. 1 1986, 1417-24. Blackburn, G. M.; Kent, D. E. J. Chem. Soc., Perkin Trans. 1 1986, 913-917. Blackburn, G. M.; Brown, D.; Martin, S. J.; Parratt, M. J. J. Chem. Soc., Perkin Trans. 1 1987, 181-186. Waschbusch, R.; Carran, J.; Savignac, P. J. Chem. Soc., Perkin Trans. 1 1997, 1135-1139. Waschbusch, R.; Carran, J.; Savignac, P. Tetrahedron 1997, 53, 6391-6400. Patois, C.; Savignac, P. J. Chem. Soc., Chem. Commun. 1993, 1711-1712. Differding, E.; Duthaler, R. O.; Krieger, A.; Rueegg, G. M.; Schmit, C. Synlett 1991, 395-396.
19. Blackburn, G. M.; Parratt, M. J. J. Chem. Soc., Perkin Trans. 1 1986, 1417-24. Blackburn, G. M.; Kent, D. E. J. Chem. Soc., Perkin Trans. 1 1986, 913-917. Blackburn, G. M.; Brown, D.; Martin, S. J.; Parratt, M. J. J. Chem. Soc., Perkin Trans. 1 1987, 181-186. Waschbusch, R.; Carran, J.; Savignac, P. J. Chem. Soc., Perkin Trans. 1 1997, 1135-1139. Waschbusch, R.; Carran, J.; Savignac, P. Tetrahedron 1997, 53, 6391-6400. Patois, C.; Savignac, P. J. Chem. Soc., Chem. Commun. 1993, 1711-1712. Differding, E.; Duthaler, R. O.; Krieger, A.; Rueegg, G. M.; Schmit, C. Synlett 1991, 395-396.
20. Blackburn, G. M.; Parratt, M. J. J. Chem. Soc., Perkin Trans. 1 1986, 1417-24. Blackburn, G. M.; Kent, D. E. J. Chem. Soc., Perkin Trans. 1 1986, 913-917. Blackburn, G. M.; Brown, D.; Martin, S. J.; Parratt, M. J. J. Chem. Soc., Perkin Trans. 1 1987, 181-186. Waschbusch, R.; Carran, J.; Savignac, P. J. Chem. Soc., Perkin Trans. 1 1997, 1135-1139. Waschbusch, R.; Carran, J.; Savignac, P. Tetrahedron 1997, 53, 6391-6400. Patois, C.; Savignac, P. J. Chem. Soc., Chem. Commun. 1993, 1711-1712. Differding, E.; Duthaler, R. O.; Krieger, A.; Rueegg, G. M.; Schmit, C. Synlett 1991, 395-396.
21. Blackburn, G. M.; Parratt, M. J. J. Chem. Soc., Perkin Trans. 1 1986, 1417-24. Blackburn, G. M.; Kent, D. E. J. Chem. Soc., Perkin Trans. 1 1986, 913-917. Blackburn, G. M.; Brown, D.; Martin, S. J.; Parratt, M. J. J. Chem. Soc., Perkin Trans. 1 1987, 181-186. Waschbusch, R.; Carran, J.; Savignac, P. J. Chem. Soc., Perkin Trans. 1 1997, 1135-1139. Waschbusch, R.; Carran, J.; Savignac, P. Tetrahedron 1997, 53, 6391-6400. Patois, C.; Savignac, P. J. Chem. Soc., Chem. Commun. 1993, 1711-1712. Differding, E.; Duthaler, R. O.; Krieger, A.; Rueegg, G. M.; Schmit, C. Synlett 1991, 395-396.
22. Blackburn, G. M.; Parratt, M. J. J. Chem. Soc., Perkin Trans. 1 1986, 1417-24. Blackburn, G. M.; Kent, D. E. J. Chem. Soc., Perkin Trans. 1 1986, 913-917. Blackburn, G. M.; Brown, D.; Martin, S. J.; Parratt, M. J. J. Chem. Soc., Perkin Trans. 1 1987, 181-186. Waschbusch, R.; Carran, J.; Savignac, P. J. Chem. Soc., Perkin Trans. 1 1997, 1135-1139. Waschbusch, R.; Carran, J.; Savignac, P. Tetrahedron 1997, 53, 6391-6400. Patois, C.; Savignac, P. J. Chem. Soc., Chem. Commun. 1993, 1711-1712. Differding, E.; Duthaler, R. O.; Krieger, A.; Rueegg, G. M.; Schmit, C. Synlett 1991, 395-396.
23. Blackburn, G. M.; Parratt, M. J. J. Chem. Soc., Perkin Trans. 1 1986, 1417-24. Blackburn, G. M.; Kent, D. E. J. Chem. Soc., Perkin Trans. 1 1986, 913-917. Blackburn, G. M.; Brown, D.; Martin, S. J.; Parratt, M. J. J. Chem. Soc., Perkin Trans. 1 1987, 181-186. Waschbusch, R.; Carran, J.; Savignac, P. J. Chem. Soc., Perkin Trans. 1 1997, 1135-1139. Waschbusch, R.; Carran, J.; Savignac, P. Tetrahedron 1997, 53, 6391-6400. Patois, C.; Savignac, P. J. Chem. Soc., Chem. Commun. 1993, 1711-1712. Differding, E.; Duthaler, R. O.; Krieger, A.; Rueegg, G. M.; Schmit, C. Synlett 1991, 395-396.
24. Selected examples include: Berkowitz, D. B.; Eggen, M.; Shen, Q.; Shoemaker, R. K. J. Org. Chem. 1996, 61, 4666-4675. Berkowitz, D. B.; Sloss, D. G. J. Org. Chem. 1995, 60, 7047-7050. Ye, B.; Burke, T. R., Jr. Tetrahedron 1996, 52, 9963-9970. Chambers, R. D.; O'Hagan, D.; Lamont, R. B.; Jain, S. C. J. Chem. Soc., Chem. Commun. 1990, 1053-1054. Chambers, R. D.; Jaouhari, R.; O'Hagan, D. J. Fluorine Chem. 1989, 44, 275-284. Waschbusch, R.; Samadi, M.; Savignac, P. J. Organomet. Chem. 1997, 529, 267-278. Lequeux, T. P.; Percy, J. M. J. Chem. Soc., Chem. Commun. 1995, 2111-2112. Lequeux, T. P.; Percy, J. M. Synlett 1995, 361-362. Yokomatsu, T.; Murano, T.; Suemune, K.; Shibuya, S. Tetrahedron 1997, 53, 815-822.
25. Selected examples include: Berkowitz, D. B.; Eggen, M.; Shen, Q.; Shoemaker, R. K. J. Org. Chem. 1996, 61, 4666-4675. Berkowitz, D. B.; Sloss, D. G. J. Org. Chem. 1995, 60, 7047-7050. Ye, B.; Burke, T. R., Jr. Tetrahedron 1996, 52, 9963-9970. Chambers, R. D.; O'Hagan, D.; Lamont, R. B.; Jain, S. C. J. Chem. Soc., Chem. Commun. 1990, 1053-1054. Chambers, R. D.; Jaouhari, R.; O'Hagan, D. J. Fluorine Chem. 1989, 44, 275-284. Waschbusch, R.; Samadi, M.; Savignac, P. J. Organomet. Chem. 1997, 529, 267-278. Lequeux, T. P.; Percy, J. M. J. Chem. Soc., Chem. Commun. 1995, 2111-2112. Lequeux, T. P.; Percy, J. M. Synlett 1995, 361-362. Yokomatsu, T.; Murano, T.; Suemune, K.; Shibuya, S. Tetrahedron 1997, 53, 815-822.
26. Selected examples include: Berkowitz, D. B.; Eggen, M.; Shen, Q.; Shoemaker, R. K. J. Org. Chem. 1996, 61, 4666-4675. Berkowitz, D. B.; Sloss, D. G. J. Org. Chem. 1995, 60, 7047-7050. Ye, B.; Burke, T. R., Jr. Tetrahedron 1996, 52, 9963-9970. Chambers, R. D.; O'Hagan, D.; Lamont, R. B.; Jain, S. C. J. Chem. Soc., Chem. Commun. 1990, 1053-1054. Chambers, R. D.; Jaouhari, R.; O'Hagan, D. J. Fluorine Chem. 1989, 44, 275-284. Waschbusch, R.; Samadi, M.; Savignac, P. J. Organomet. Chem. 1997, 529, 267-278. Lequeux, T. P.; Percy, J. M. J. Chem. Soc., Chem. Commun. 1995, 2111-2112. Lequeux, T. P.; Percy, J. M. Synlett 1995, 361-362. Yokomatsu, T.; Murano, T.; Suemune, K.; Shibuya, S. Tetrahedron 1997, 53, 815-822.
27. Selected examples include: Berkowitz, D. B.; Eggen, M.; Shen, Q.; Shoemaker, R. K. J. Org. Chem. 1996, 61, 4666-4675. Berkowitz, D. B.; Sloss, D. G. J. Org. Chem. 1995, 60, 7047-7050. Ye, B.; Burke, T. R., Jr. Tetrahedron 1996, 52, 9963-9970. Chambers, R. D.; O'Hagan, D.; Lamont, R. B.; Jain, S. C. J. Chem. Soc., Chem. Commun. 1990, 1053-1054. Chambers, R. D.; Jaouhari, R.; O'Hagan, D. J. Fluorine Chem. 1989, 44, 275-284. Waschbusch, R.; Samadi, M.; Savignac, P. J. Organomet. Chem. 1997, 529, 267-278. Lequeux, T. P.; Percy, J. M. J. Chem. Soc., Chem. Commun. 1995, 2111-2112. Lequeux, T. P.; Percy, J. M. Synlett 1995, 361-362. Yokomatsu, T.; Murano, T.; Suemune, K.; Shibuya, S. Tetrahedron 1997, 53, 815-822.
28. Selected examples include: Berkowitz, D. B.; Eggen, M.; Shen, Q.; Shoemaker, R. K. J. Org. Chem. 1996, 61, 4666-4675. Berkowitz, D. B.; Sloss, D. G. J. Org. Chem. 1995, 60, 7047-7050. Ye, B.; Burke, T. R., Jr. Tetrahedron 1996, 52, 9963-9970. Chambers, R. D.; O'Hagan, D.; Lamont, R. B.; Jain, S. C. J. Chem. Soc., Chem. Commun. 1990, 1053-1054. Chambers, R. D.; Jaouhari, R.; O'Hagan, D. J. Fluorine Chem. 1989, 44, 275-284. Waschbusch, R.; Samadi, M.; Savignac, P. J. Organomet. Chem. 1997, 529, 267-278. Lequeux, T. P.; Percy, J. M. J. Chem. Soc., Chem. Commun. 1995, 2111-2112. Lequeux, T. P.; Percy, J. M. Synlett 1995, 361-362. Yokomatsu, T.; Murano, T.; Suemune, K.; Shibuya, S. Tetrahedron 1997, 53, 815-822.
29. Selected examples include: Berkowitz, D. B.; Eggen, M.; Shen, Q.; Shoemaker, R. K. J. Org. Chem. 1996, 61, 4666-4675. Berkowitz, D. B.; Sloss, D. G. J. Org. Chem. 1995, 60, 7047-7050. Ye, B.; Burke, T. R., Jr. Tetrahedron 1996, 52, 9963-9970. Chambers, R. D.; O'Hagan, D.; Lamont, R. B.; Jain, S. C. J. Chem. Soc., Chem. Commun. 1990, 1053-1054. Chambers, R. D.; Jaouhari, R.; O'Hagan, D. J. Fluorine Chem. 1989, 44, 275-284. Waschbusch, R.; Samadi, M.; Savignac, P. J. Organomet. Chem. 1997, 529, 267-278. Lequeux, T. P.; Percy, J. M. J. Chem. Soc., Chem. Commun. 1995, 2111-2112. Lequeux, T. P.; Percy, J. M. Synlett 1995, 361-362. Yokomatsu, T.; Murano, T.; Suemune, K.; Shibuya, S. Tetrahedron 1997, 53, 815-822.
30. Selected examples include: Berkowitz, D. B.; Eggen, M.; Shen, Q.; Shoemaker, R. K. J. Org. Chem. 1996, 61, 4666-4675. Berkowitz, D. B.; Sloss, D. G. J. Org. Chem. 1995, 60, 7047-7050. Ye, B.; Burke, T. R., Jr. Tetrahedron 1996, 52, 9963-9970. Chambers, R. D.; O'Hagan, D.; Lamont, R. B.; Jain, S. C. J. Chem. Soc., Chem. Commun. 1990, 1053-1054. Chambers, R. D.; Jaouhari, R.; O'Hagan, D. J. Fluorine Chem. 1989, 44, 275-284. Waschbusch, R.; Samadi, M.; Savignac, P. J. Organomet. Chem. 1997, 529, 267-278. Lequeux, T. P.; Percy, J. M. J. Chem. Soc., Chem. Commun. 1995, 2111-2112. Lequeux, T. P.; Percy, J. M. Synlett 1995, 361-362. Yokomatsu, T.; Murano, T.; Suemune, K.; Shibuya, S. Tetrahedron 1997, 53, 815-822.
31. Selected examples include: Berkowitz, D. B.; Eggen, M.; Shen, Q.; Shoemaker, R. K. J. Org. Chem. 1996, 61, 4666-4675. Berkowitz, D. B.; Sloss, D. G. J. Org. Chem. 1995, 60, 7047-7050. Ye, B.; Burke, T. R., Jr. Tetrahedron 1996, 52, 9963-9970. Chambers, R. D.; O'Hagan, D.; Lamont, R. B.; Jain, S. C. J. Chem. Soc., Chem. Commun. 1990, 1053-1054. Chambers, R. D.; Jaouhari, R.; O'Hagan, D. J. Fluorine Chem. 1989, 44, 275-284. Waschbusch, R.; Samadi, M.; Savignac, P. J. Organomet. Chem. 1997, 529, 267-278. Lequeux, T. P.; Percy, J. M. J. Chem. Soc., Chem. Commun. 1995, 2111-2112. Lequeux, T. P.; Percy, J. M. Synlett 1995, 361-362. Yokomatsu, T.; Murano, T.; Suemune, K.; Shibuya, S. Tetrahedron 1997, 53, 815-822.
32. Selected examples include: Berkowitz, D. B.; Eggen, M.; Shen, Q.; Shoemaker, R. K. J. Org. Chem. 1996, 61, 4666-4675. Berkowitz, D. B.; Sloss, D. G. J. Org. Chem. 1995, 60, 7047-7050. Ye, B.; Burke, T. R., Jr. Tetrahedron 1996, 52, 9963-9970. Chambers, R. D.; O'Hagan, D.; Lamont, R. B.; Jain, S. C. J. Chem. Soc., Chem. Commun. 1990, 1053-1054. Chambers, R. D.; Jaouhari, R.; O'Hagan, D. J. Fluorine Chem. 1989, 44, 275-284. Waschbusch, R.; Samadi, M.; Savignac, P. J. Organomet. Chem. 1997, 529, 267-278. Lequeux, T. P.; Percy, J. M. J. Chem. Soc., Chem. Commun. 1995, 2111-2112. Lequeux, T. P.; Percy, J. M. Synlett 1995, 361-362. Yokomatsu, T.; Murano, T.; Suemune, K.; Shibuya, S. Tetrahedron 1997, 53, 815-822.
33. Phillion, D. P.; Cleary, D. G. J. Org. Chem. 1992, 57, 2763-2764. Yokomatsu, T.; Suemune, K.; Murano, T.; Shibuya, S. J. Org. Chem. 1996, 61, 7207-7211. Blades, K.; Lequeux, T. P.; Percy, J. M. Chem. Commun. 1996, 1457-1458. Halazy, S.; Gross-Berges, V. J. Chem. Soc., Chem. Commun. 1992, 743-745. Yang, Z. Y.; Burton, D. J. J. Org. Chem. 1992, 57, 4676-83.
34. Phillion, D. P.; Cleary, D. G. J. Org. Chem. 1992, 57, 2763- 2764. Yokomatsu, T.; Suemune, K.; Murano, T.; Shibuya, S. J. Org. Chem. 1996, 61, 7207-7211. Blades, K.; Lequeux, T. P.; Percy, J. M. Chem. Commun. 1996, 1457-1458. Halazy, S.; Gross-Berges, V. J. Chem. Soc., Chem. Commun. 1992, 743-745. Yang, Z. Y.; Burton, D. J. J. Org. Chem. 1992, 57, 4676-83.
35. Phillion, D. P.; Cleary, D. G. J. Org. Chem. 1992, 57, 2763- 2764. Yokomatsu, T.; Suemune, K.; Murano, T.; Shibuya, S. J. Org. Chem. 1996, 61, 7207-7211. Blades, K.; Lequeux, T. P.; Percy, J. M. Chem. Commun. 1996, 1457-1458. Halazy, S.; Gross-Berges, V. J. Chem. Soc., Chem. Commun. 1992, 743-745. Yang, Z. Y.; Burton, D. J. J. Org. Chem. 1992, 57, 4676-83.
36. Phillion, D. P.; Cleary, D. G. J. Org. Chem. 1992, 57, 2763- 2764. Yokomatsu, T.; Suemune, K.; Murano, T.; Shibuya, S. J. Org. Chem. 1996, 61, 7207-7211. Blades, K.; Lequeux, T. P.; Percy, J. M. Chem. Commun. 1996, 1457-1458. Halazy, S.; Gross-Berges, V. J. Chem. Soc., Chem. Commun. 1992, 743-745. Yang, Z. Y.; Burton, D. J. J. Org. Chem. 1992, 57, 4676-83.
37. Phillion, D. P.; Cleary, D. G. J. Org. Chem. 1992, 57, 2763- 2764. Yokomatsu, T.; Suemune, K.; Murano, T.; Shibuya, S. J. Org. Chem. 1996, 61, 7207-7211. Blades, K.; Lequeux, T. P.; Percy, J. M. Chem. Commun. 1996, 1457-1458. Halazy, S.; Gross-Berges, V. J. Chem. Soc., Chem. Commun. 1992, 743-745. Yang, Z. Y.; Burton, D. J. J. Org. Chem. 1992, 57, 4676-83.
38. Benayoud, F.; Hammond, G. B. J. Chem. Soc., Chem. Commun. 1996, 1447-1448.
39. Thatcher, G. R. J.; Campbell, A. S. J. Org. Chem. 1993, 58, 2272-2281. Nieschalk, J.; Batsanov, A. S.; O'Hagan, D.; Howard, J. A. K. Tetrahedron 1996, 52, 165-176.
40. Thatcher, G. R. J.; Campbell, A. S. J. Org. Chem. 1993, 58, 2272-2281. Nieschalk, J.; Batsanov, A. S.; O'Hagan, D.; Howard, J. A. K. Tetrahedron 1996, 52, 165-176.
41. (a) Sanders, T. C.; Hammond, G. B. J. Org. Chem. 1993, 58, 8-5599.
42. (b) Benayoud, F.; deMendonca, D. J.; Digits, C. A.; Moniz, G. A.; Sanders, T. C.; Hammond, G. B. J. Org. Chem. 1996, 61, 5159-5164.
43. Zhang, X.; Qiu, W.; Burton, D. J. Tetrahedron Lett. 1999, 40, 2681-2684.
44. Enantiocontrolled Synthesis of Fluoro-Organic Compounds; Soloshonok, V. A., Ed.; Wiley & Sons: West Sussex, 1999. Review on catalytic asymmetric synthesis: Iseki, K. Tetrahedron 1998, 54, 13887-13914. Other selected examples: Gree, D. M.; Kermarrec, C. J. M.; Martelli, J. T.; Gree, R. L. J. Org. Chem. 1996, 61, 1918-1919. Myers, A. G.; McKinstry, L.; Gleason, J. L. Tetrahedron Lett. 1997, 38, 7037-7040. Marson, C. M.; Melling, R. C. J. Chem. Soc.,. Chem. Commun. 1998, 1223-1224.
45. Enantiocontrolled Synthesis of Fluoro-Organic Compounds; Soloshonok, V. A., Ed.; Wiley & Sons: West Sussex, 1999. Review on catalytic asymmetric synthesis: Iseki, K. Tetrahedron 1998, 54, 13887-13914. Other selected examples: Gree, D. M.; Kermarrec, C. J. M.; Martelli, J. T.; Gree, R. L. J. Org. Chem. 1996, 61, 1918-1919. Myers, A. G.; McKinstry, L.; Gleason, J. L. Tetrahedron Lett. 1997, 38, 7037-7040. Marson, C. M.; Melling, R. C. J. Chem. Soc.,. Chem. Commun. 1998, 1223-1224.
46. Enantiocontrolled Synthesis of Fluoro-Organic Compounds; Soloshonok, V. A., Ed.; Wiley & Sons: West Sussex, 1999. Review on catalytic asymmetric synthesis: Iseki, K. Tetrahedron 1998, 54, 13887-13914. Other selected examples: Gree, D. M.; Kermarrec, C. J. M.; Martelli, J. T.; Gree, R. L. J. Org. Chem. 1996, 61, 1918-1919. Myers, A. G.; McKinstry, L.; Gleason, J. L. Tetrahedron Lett. 1997, 38, 7037-7040. Marson, C. M.; Melling, R. C. J. Chem. Soc.,. Chem. Commun. 1998, 1223-1224.
47. Enantiocontrolled Synthesis of Fluoro-Organic Compounds; Soloshonok, V. A., Ed.; Wiley & Sons: West Sussex, 1999. Review on catalytic asymmetric synthesis: Iseki, K. Tetrahedron 1998, 54, 13887-13914. Other selected examples: Gree, D. M.; Kermarrec, C. J. M.; Martelli, J. T.; Gree, R. L. J. Org. Chem. 1996, 61, 1918-1919. Myers, A. G.; McKinstry, L.; Gleason, J. L. Tetrahedron Lett. 1997, 38, 7037-7040. Marson, C. M.; Melling, R. C. J. Chem. Soc.,. Chem. Commun. 1998, 1223-1224.
48. Enantiocontrolled Synthesis of Fluoro-Organic Compounds; Soloshonok, V. A., Ed.; Wiley & Sons: West Sussex, 1999. Review on catalytic asymmetric synthesis: Iseki, K. Tetrahedron 1998, 54, 13887-13914. Other selected examples: Gree, D. M.; Kermarrec, C. J. M.; Martelli, J. T.; Gree, R. L. J. Org. Chem. 1996, 61, 1918-1919. Myers, A. G.; McKinstry, L.; Gleason, J. L. Tetrahedron Lett. 1997, 38, 7037-7040. Marson, C. M.; Melling, R. C. J. Chem. Soc.,. Chem. Commun. 1998, 1223-1224.
49. Benayoud, F.; Chen, L.; Moniz, G. A.; Zapata, A. J.; Hammond, G. B. Tetrahedron 1998, 54, 15541-15554.
50. For example, silyynolates have been isolated, whereas their alkylcounterparts remain highly unstable: Kai, H.; Iwamoto, K.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 1996, 118, 7634-7635. For a recent review of the TIPS group in organic chemistry, see: Rücker, C. Chem. Rev. 1995, 95, 1009-1064.
51. For example, silyynolates have been isolated, whereas their alkylcounterparts remain highly unstable: Kai, H.; Iwamoto, K.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 1996, 118, 7634-7635. For a recent review of the TIPS group in organic chemistry, see: Rücker, C. Chem. Rev. 1995, 95, 1009-1064.
52. Danheiser, R. L.; Stoner, E. J.; Koyama, H.; Yamashita, D. S.; Klade, C. A. J. Am. Chem. Soc. 1989, 111, 4407-4413.
53. Dess-Martin oxidation furnished the corresponding aldehyde which was then converted to 5 using diethyl phosphite and solid KF. See also ref 12b.
54. Gibson, A. W.; Humphrey, G. R.; Kennedy, D. J.; Wright, S. H. B. Synthesis 1991, 414-416.
55. Reference 3a, pp 475-490.
56. Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863-927.
57. Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453-6518. Nicolaou, K. C.; Smith, A. L. In Modern Acetylene Chemistry; Stang, P. J., Diederich, F., Eds.; VCH: Weinheim, Germany, 1995; pp 203-283.
58. Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453-6518. Nicolaou, K. C.; Smith, A. L. In Modern Acetylene Chemistry; Stang, P. J., Diederich, F., Eds.; VCH: Weinheim, Germany, 1995; pp 203-283.
59. Benayoud, F.; Sanders, T.; Hammond, G. B. Unpublished results.
60. Still, W. C.; Gennari, C. Tetrahedron Lett. 1983, 24, 4405-4408.
61. Gao, L.-X.; Murai, A. Tetrahedron Lett. 1992, 33, 4349-4352.
62. Corey, E. J.; Rucker, C. Tetrahedron Lett. 1982, 23, 719-722.
63. Hatanaka, Y.; Matsui, K.; Hiyama, T. Tetrahedron Lett. 1989, 30, 2403-2406.
64. Thorand, S.; Krause, N. J. Org. Chem. 1998, 63, 8551-8553.
65. Wipf, P.; Jahn, H. Tetrahedron 1996, 52, 12853-12910.
66. Nakamura, H.; Aoyagi, K.; Yamamoto, Y. J. Am. Chem. Soc. 1998, 120, 1167-1171.
67. Trost, B. M.; Michellys, P.-Y.; Gerusz, V. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 1750-1752. Morwick, T. M.; Paquette, L. A. J. Org. Chem. 1997, 62, 627-635.
68. Trost, B. M.; Michellys, P.-Y.; Gerusz, V. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 1750-1752. Morwick, T. M.; Paquette, L. A. J. Org. Chem. 1997, 62, 627-635.
69. Mikami, K.; Yoshida, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 858-860.
70. Schuster, H. F.; Coppola, G. M. Allenes in Organic Synthesis; John Wiley: New York, 1984.
71. Xu, Z.-Q.; Zemlicka, J. Tetrahedron 1997, 53, 5389-5396.
72. For a recent review, see: Minami, T.; J., M. Synthesis 1992, 339-349. For selected recent examples, see: Nagaoka, Y.; Tomioka, K. J. Org. Chem. 1998, 63, 6428-6429. Cristau, H.-J.; Mbianda, X. Y.; Beziat, Y.; Gasc, M.-B. J. Organomet. Chem. 1997, 529, 301-311. Kim, D. Y.; Rhie, D. Y. Tetrahedron 1997, 53, 13603-13608. Xu, Y.; Flavin, M. T.; Xu, Z.-Q. J. Org. Chem. 1996, 61, 7697-7701. Besson, L.; Gore, J.; Cazes, B. Tetrahedron Lett. 1995, 36, 3857-3860. Aboujaoude, E. E.; Lietje, S.; Collignon, N. Synthesis 1986, 934-937. Gerber, J. P. M., T. A.; Wagener, C. C. P.; Zwierzak, A. Heteroatom Chem. 1991, 2, 643-649.
73. For a recent review, see: Minami, T.; J., M. Synthesis 1992, 339-349. For selected recent examples, see: Nagaoka, Y.; Tomioka, K. J. Org. Chem. 1998, 63, 6428-6429. Cristau, H.-J.; Mbianda, X. Y.; Beziat, Y.; Gasc, M.-B. J. Organomet. Chem. 1997, 529, 301-311. Kim, D. Y.; Rhie, D. Y. Tetrahedron 1997, 53, 13603-13608. Xu, Y.; Flavin, M. T.; Xu, Z.-Q. J. Org. Chem. 1996, 61, 7697-7701. Besson, L.; Gore, J.; Cazes, B. Tetrahedron Lett. 1995, 36, 3857-3860. Aboujaoude, E. E.; Lietje, S.; Collignon, N. Synthesis 1986, 934-937. Gerber, J. P. M., T. A.; Wagener, C. C. P.; Zwierzak, A. Heteroatom Chem. 1991, 2, 643-649.
74. For a recent review, see: Minami, T.; J., M. Synthesis 1992, 339-349. For selected recent examples, see: Nagaoka, Y.; Tomioka, K. J. Org. Chem. 1998, 63, 6428-6429. Cristau, H.-J.; Mbianda, X. Y.; Beziat, Y.; Gasc, M.-B. J. Organomet. Chem. 1997, 529, 301-311. Kim, D. Y.; Rhie, D. Y. Tetrahedron 1997, 53, 13603-13608. Xu, Y.; Flavin, M. T.; Xu, Z.-Q. J. Org. Chem. 1996, 61, 7697-7701. Besson, L.; Gore, J.; Cazes, B. Tetrahedron Lett. 1995, 36, 3857-3860. Aboujaoude, E. E.; Lietje, S.; Collignon, N. Synthesis 1986, 934-937. Gerber, J. P. M., T. A.; Wagener, C. C. P.; Zwierzak, A. Heteroatom Chem. 1991, 2, 643-649.
75. For a recent review, see: Minami, T.; J., M. Synthesis 1992, 339-349. For selected recent examples, see: Nagaoka, Y.; Tomioka, K. J. Org. Chem. 1998, 63, 6428-6429. Cristau, H.-J.; Mbianda, X. Y.; Beziat, Y.; Gasc, M.-B. J. Organomet. Chem. 1997, 529, 301-311. Kim, D. Y.; Rhie, D. Y. Tetrahedron 1997, 53, 13603-13608. Xu, Y.; Flavin, M. T.; Xu, Z.-Q. J. Org. Chem. 1996, 61, 7697-7701. Besson, L.; Gore, J.; Cazes, B. Tetrahedron Lett. 1995, 36, 3857-3860. Aboujaoude, E. E.; Lietje, S.; Collignon, N. Synthesis 1986, 934-937. Gerber, J. P. M., T. A.; Wagener, C. C. P.; Zwierzak, A. Heteroatom Chem. 1991, 2, 643-649.
76. For a recent review, see: Minami, T.; J., M. Synthesis 1992, 339-349. For selected recent examples, see: Nagaoka, Y.; Tomioka, K. J. Org. Chem. 1998, 63, 6428-6429. Cristau, H.-J.; Mbianda, X. Y.; Beziat, Y.; Gasc, M.-B. J. Organomet. Chem. 1997, 529, 301-311. Kim, D. Y.; Rhie, D. Y. Tetrahedron 1997, 53, 13603-13608. Xu, Y.; Flavin, M. T.; Xu, Z.-Q. J. Org. Chem. 1996, 61, 7697-7701. Besson, L.; Gore, J.; Cazes, B. Tetrahedron Lett. 1995, 36, 3857-3860. Aboujaoude, E. E.; Lietje, S.; Collignon, N. Synthesis 1986, 934-937. Gerber, J. P. M., T. A.; Wagener, C. C. P.; Zwierzak, A. Heteroatom Chem. 1991, 2, 643-649.
77. For a recent review, see: Minami, T.; J., M. Synthesis 1992, 339-349. For selected recent examples, see: Nagaoka, Y.; Tomioka, K. J. Org. Chem. 1998, 63, 6428-6429. Cristau, H.-J.; Mbianda, X. Y.; Beziat, Y.; Gasc, M.-B. J. Organomet. Chem. 1997, 529, 301-311. Kim, D. Y.; Rhie, D. Y. Tetrahedron 1997, 53, 13603-13608. Xu, Y.; Flavin, M. T.; Xu, Z.-Q. J. Org. Chem. 1996, 61, 7697-7701. Besson, L.; Gore, J.; Cazes, B. Tetrahedron Lett. 1995, 36, 3857-3860. Aboujaoude, E. E.; Lietje, S.; Collignon, N. Synthesis 1986, 934-937. Gerber, J. P. M., T. A.; Wagener, C. C. P.; Zwierzak, A. Heteroatom Chem. 1991, 2, 643-649.
78. For a recent review, see: Minami, T.; J., M. Synthesis 1992, 339-349. For selected recent examples, see: Nagaoka, Y.; Tomioka, K. J. Org. Chem. 1998, 63, 6428-6429. Cristau, H.-J.; Mbianda, X. Y.; Beziat, Y.; Gasc, M.-B. J. Organomet. Chem. 1997, 529, 301-311. Kim, D. Y.; Rhie, D. Y. Tetrahedron 1997, 53, 13603-13608. Xu, Y.; Flavin, M. T.; Xu, Z.-Q. J. Org. Chem. 1996, 61, 7697-7701. Besson, L.; Gore, J.; Cazes, B. Tetrahedron Lett. 1995, 36, 3857-3860. Aboujaoude, E. E.; Lietje, S.; Collignon, N. Synthesis 1986, 934-937. Gerber, J. P. M., T. A.; Wagener, C. C. P.; Zwierzak, A. Heteroatom Chem. 1991, 2, 643-649.
79. For a recent review, see: Minami, T.; J., M. Synthesis 1992, 339-349. For selected recent examples, see: Nagaoka, Y.; Tomioka, K. J. Org. Chem. 1998, 63, 6428-6429. Cristau, H.-J.; Mbianda, X. Y.; Beziat, Y.; Gasc, M.-B. J. Organomet. Chem. 1997, 529, 301-311. Kim, D. Y.; Rhie, D. Y. Tetrahedron 1997, 53, 13603-13608. Xu, Y.; Flavin, M. T.; Xu, Z.-Q. J. Org. Chem. 1996, 61, 7697-7701. Besson, L.; Gore, J.; Cazes, B. Tetrahedron Lett. 1995, 36, 3857-3860. Aboujaoude, E. E.; Lietje, S.; Collignon, N. Synthesis 1986, 934-937. Gerber, J. P. M., T. A.; Wagener, C. C. P.; Zwierzak, A. Heteroatom Chem. 1991, 2, 643-649.
80. Schmitt, L.; Cavusoglu, N.; Spiess, B.; Schlewer, G. Tetrahedron Lett. 1998, 39, 4009-4012. Halazy, S.; Eggenspiller, A.; Ehrhard, A.; Danzin, C. Bioorg. Med. Chem. Lett. 1992, 2, 407-410.
81. Schmitt, L.; Cavusoglu, N.; Spiess, B.; Schlewer, G. Tetrahedron Lett. 1998, 39, 4009-4012. Halazy, S.; Eggenspiller, A.; Ehrhard, A.; Danzin, C. Bioorg. Med. Chem. Lett. 1992, 2, 407-410.
82. Waschbusch, R.; Carran, J.; Savignac, P. Tetrahedron 1996, 52, 14199-14216. Keeney, A.; Nieschalk, J.; O'Hagan, D. J. Fluorine Chem. 1996, 80, 59-62.
83. Waschbusch, R.; Carran, J.; Savignac, P. Tetrahedron 1996, 52, 14199-14216. Keeney, A.; Nieschalk, J.; O'Hagan, D. J. Fluorine Chem. 1996, 80, 59-62.
84. Gross, R. S.; Mehdi, S.; McCarthy, J. R. Tetrahedron Lett. 1993, 34, 7197-200.
85. For a recent review see: Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S. R.; Earl, R. A.; Guedj, R. Tetrahedron 1994, 50, 10611-10670. Selected examples include: Chen, W.; Flavin, M. T.; Filler, R.; Xu, Z.-Q. Tetrahedron Lett. 1996, 37, 8975-8978. Matulic- Adamic, J.; Haeberli, P.; Usman, N. J. Org. Chem. 1995, 60, 2563- 2569. Matulic-Adamic, J.; Usman, N. Tetrahedron Lett. 1994, 35, 3227-3230. Matulic-Adamic, J.; Rosenberg, I.; Arzumanov, A. A.; Dyatkina, N. B.; Shirokova, E. A.; Krayevsky, A. A.; Watanabe, K. A. Nucleosides Nucleotides 1993, 12, 1085-1092. Arabshahi, L.; Khan, N. N.; Butler, M.; Noonan, T.; Brown, N. C.; Wright, G. E. Biochemistry 1990, 29, 6820-6826. Bergstrom, D. E.; Shum, P. W. J. Org. Chem. 1988, 53, 3953-3958.
86. For a recent review see: Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S. R.; Earl, R. A.; Guedj, R. Tetrahedron 1994, 50, 10611-10670. Selected examples include: Chen, W.; Flavin, M. T.; Filler, R.; Xu, Z.-Q. Tetrahedron Lett. 1996, 37, 8975-8978. Matulic- Adamic, J.; Haeberli, P.; Usman, N. J. Org. Chem. 1995, 60, 2563- 2569. Matulic-Adamic, J.; Usman, N. Tetrahedron Lett. 1994, 35, 3227-3230. Matulic-Adamic, J.; Rosenberg, I.; Arzumanov, A. A.; Dyatkina, N. B.; Shirokova, E. A.; Krayevsky, A. A.; Watanabe, K. A. Nucleosides Nucleotides 1993, 12, 1085-1092. Arabshahi, L.; Khan, N. N.; Butler, M.; Noonan, T.; Brown, N. C.; Wright, G. E. Biochemistry 1990, 29, 6820-6826. Bergstrom, D. E.; Shum, P. W. J. Org. Chem. 1988, 53, 3953-3958.
87. For a recent review see: Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S. R.; Earl, R. A.; Guedj, R. Tetrahedron 1994, 50, 10611-10670. Selected examples include: Chen, W.; Flavin, M. T.; Filler, R.; Xu, Z.-Q. Tetrahedron Lett. 1996, 37, 8975-8978. Matulic-Adamic, J.; Haeberli, P.; Usman, N. J. Org. Chem. 1995, 60, 2563-2569. Matulic-Adamic, J.; Usman, N. Tetrahedron Lett. 1994, 35, 3227-3230. Matulic-Adamic, J.; Rosenberg, I.; Arzumanov, A. A.; Dyatkina, N. B.; Shirokova, E. A.; Krayevsky, A. A.; Watanabe, K. A. Nucleosides Nucleotides 1993, 12, 1085-1092. Arabshahi, L.; Khan, N. N.; Butler, M.; Noonan, T.; Brown, N. C.; Wright, G. E. Biochemistry 1990, 29, 6820-6826. Bergstrom, D. E.; Shum, P. W. J. Org. Chem. 1988, 53, 3953-3958.
88. For a recent review see: Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S. R.; Earl, R. A.; Guedj, R. Tetrahedron 1994, 50, 10611-10670. Selected examples include: Chen, W.; Flavin, M. T.; Filler, R.; Xu, Z.-Q. Tetrahedron Lett. 1996, 37, 8975-8978. Matulic- Adamic, J.; Haeberli, P.; Usman, N. J. Org. Chem. 1995, 60, 2563- 2569. Matulic-Adamic, J.; Usman, N. Tetrahedron Lett. 1994, 35, 3227-3230. Matulic-Adamic, J.; Rosenberg, I.; Arzumanov, A. A.; Dyatkina, N. B.; Shirokova, E. A.; Krayevsky, A. A.; Watanabe, K. A. Nucleosides Nucleotides 1993, 12, 1085-1092. Arabshahi, L.; Khan, N. N.; Butler, M.; Noonan, T.; Brown, N. C.; Wright, G. E. Biochemistry 1990, 29, 6820-6826. Bergstrom, D. E.; Shum, P. W. J. Org. Chem. 1988, 53, 3953-3958.
89. For a recent review see: Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S. R.; Earl, R. A.; Guedj, R. Tetrahedron 1994, 50, 10611-10670. Selected examples include: Chen, W.; Flavin, M. T.; Filler, R.; Xu, Z.-Q. Tetrahedron Lett. 1996, 37, 8975-8978. Matulic- Adamic, J.; Haeberli, P.; Usman, N. J. Org. Chem. 1995, 60, 2563- 2569. Matulic-Adamic, J.; Usman, N. Tetrahedron Lett. 1994, 35, 3227-3230. Matulic-Adamic, J.; Rosenberg, I.; Arzumanov, A. A.; Dyatkina, N. B.; Shirokova, E. A.; Krayevsky, A. A.; Watanabe, K. A. Nucleosides Nucleotides 1993, 12, 1085-1092. Arabshahi, L.; Khan, N. N.; Butler, M.; Noonan, T.; Brown, N. C.; Wright, G. E. Biochemistry 1990, 29, 6820-6826. Bergstrom, D. E.; Shum, P. W. J. Org. Chem. 1988, 53, 3953-3958.
90. For a recent review see: Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S. R.; Earl, R. A.; Guedj, R. Tetrahedron 1994, 50, 10611-10670. Selected examples include: Chen, W.; Flavin, M. T.; Filler, R.; Xu, Z.-Q. Tetrahedron Lett. 1996, 37, 8975-8978. Matulic- Adamic, J.; Haeberli, P.; Usman, N. J. Org. Chem. 1995, 60, 2563- 2569. Matulic-Adamic, J.; Usman, N. Tetrahedron Lett. 1994, 35, 3227-3230. Matulic-Adamic, J.; Rosenberg, I.; Arzumanov, A. A.; Dyatkina, N. B.; Shirokova, E. A.; Krayevsky, A. A.; Watanabe, K. A. Nucleosides Nucleotides 1993, 12, 1085-1092. Arabshahi, L.; Khan, N. N.; Butler, M.; Noonan, T.; Brown, N. C.; Wright, G. E. Biochemistry 1990, 29, 6820-6826. Bergstrom, D. E.; Shum, P. W. J. Org. Chem. 1988, 53, 3953-3958.
91. For a recent review see: Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S. R.; Earl, R. A.; Guedj, R. Tetrahedron 1994, 50, 10611-10670. Selected examples include: Chen, W.; Flavin, M. T.; Filler, R.; Xu, Z.-Q. Tetrahedron Lett. 1996, 37, 8975-8978. Matulic- Adamic, J.; Haeberli, P.; Usman, N. J. Org. Chem. 1995, 60, 2563- 2569. Matulic-Adamic, J.; Usman, N. Tetrahedron Lett. 1994, 35, 3227-3230. Matulic-Adamic, J.; Rosenberg, I.; Arzumanov, A. A.; Dyatkina, N. B.; Shirokova, E. A.; Krayevsky, A. A.; Watanabe, K. A. Nucleosides Nucleotides 1993, 12, 1085-1092. Arabshahi, L.; Khan, N. N.; Butler, M.; Noonan, T.; Brown, N. C.; Wright, G. E. Biochemistry 1990, 29, 6820-6826. Bergstrom, D. E.; Shum, P. W. J. Org. Chem. 1988, 53, 3953-3958.
92. Winter, H.; Maeda, Y.; Uchida, H.; Mitsuya, H.; Zemlicka, J. J. Med. Chem. 1997, 40 2191-2195. Megati, S.; Phadtare, S.; Zemlicka, J. J. Org. Chem. 1992, 57, 2320-2327.
93. Winter, H.; Maeda, Y.; Uchida, H.; Mitsuya, H.; Zemlicka, J. J. Med. Chem. 1997, 40 2191-2195. Megati, S.; Phadtare, S.; Zemlicka, J. J. Org. Chem. 1992, 57, 2320-2327.
94. Allylamines are present in naturally occurring substances and can be considered vinylogous polypeptides. See: Ofial, A. R.; Mayr, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 143-145. Palacios, F.; Aparicio, D.; Garcia, J. Tetrahedron 1996, 52, 9609-9628 and references therein.
95. Allylamines are present in naturally occurring substances and can be considered vinylogous polypeptides. See: Ofial, A. R.; Mayr, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 143-145. Palacios, F.; Aparicio, D.; Garcia, J. Tetrahedron 1996, 52, 9609-9628 and references therein.
96. For details regarding the X-ray crystal structure of 13b,c and 14a, see the Supporting Information.
97. Palacios, F.; Ochoa de Retana, A. M.; Oyarzabal, J. Tetrahedron 1999, 55, 3091-3104.
98. Park, H. M.; Uegaki, T.; Konno, T.; Ishihara, T.; Yamanaka, H. Tetrahedron Lett. 1999, 40, 2985-2988.
99. For a recent review, see: Dolbier, J. W. R. Acc. Chem. Res. 1991, 24, 63-69. Also: Jung, M. E.; Nishimura, N. J. Am. Chem. Soc. 1999, 121, 3529-3530. Xu, Z.; Lu, X. Tetrahedron Lett. 1999, 40, 549-552.
100. For a recent review, see: Dolbier, J. W. R. Acc. Chem. Res. 1991, 24, 63-69. Also: Jung, M. E.; Nishimura, N. J. Am. Chem. Soc. 1999, 121, 3529-3530. Xu, Z.; Lu, X. Tetrahedron Lett. 1999, 40, 549-552.
101. For a recent review, see: Dolbier, J. W. R. Acc. Chem. Res. 1991, 24, 63-69. Also: Jung, M. E.; Nishimura, N. J. Am. Chem. Soc. 1999, 121, 3529-3530. Xu, Z.; Lu, X. Tetrahedron Lett. 1999, 40, 549-552.
102. Weislow, O. W.; Kiser, R.; Fine, D.; Bader, J.; Shoemaker, R. H.; Boyd, M. R. J. Natl. Cancer Inst. 1989, 81, 577-586.