Synthesis and Reactions of 3-(Nosyloxy)-2-keto Esters

Journal of Organic Chemistry

Volumn 62, Issue 8, 1997, Pages 2458-2465

  Hoffman, Robert V ^a   Catherine Johnson, M ^a   Okonya, John F ^a  

^a NEW MEXICO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000404299     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962206h     Document Type: Article

References (50)

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24. The hydration of electrophilic ketones has been of recent interest, (a) Krois, D.; Langer, E.; Lehner, H. Tetrahedron 1980, 36, 1345. (b) Ocain, T. D.; Rich, D. H. J. Med. Chem. 1992, 35, 451. (c) Yuan, W.; Munoz, B.; Wong, C.-H. J. Med. Chem. 1993, 36, 211. (d) Peet, N. P.; Burkhart, J. P.; Angelastro, M. R.; Giroux, E. L.; Mehdi, S.; Bey, P.; Kolb, M.; Neises, B.; Schiriin, D. J. Med. Chem. 1990, 33, 394. (e) Gelb, M. H.; Svaren, J. P.; Abeles, R. H. Biochemistry 1985, 24, 1813. (f) Parisi, M. F.; Abeles, R. H. Biochemistry 1992, 31, 9429.
25. The hydration of electrophilic ketones has been of recent interest, (a) Krois, D.; Langer, E.; Lehner, H. Tetrahedron 1980, 36, 1345. (b) Ocain, T. D.; Rich, D. H. J. Med. Chem. 1992, 35, 451. (c) Yuan, W.; Munoz, B.; Wong, C.-H. J. Med. Chem. 1993, 36, 211. (d) Peet, N. P.; Burkhart, J. P.; Angelastro, M. R.; Giroux, E. L.; Mehdi, S.; Bey, P.; Kolb, M.; Neises, B.; Schiriin, D. J. Med. Chem. 1990, 33, 394. (e) Gelb, M. H.; Svaren, J. P.; Abeles, R. H. Biochemistry 1985, 24, 1813. (f) Parisi, M. F.; Abeles, R. H. Biochemistry 1992, 31, 9429.
26. The hydration of electrophilic ketones has been of recent interest, (a) Krois, D.; Langer, E.; Lehner, H. Tetrahedron 1980, 36, 1345. (b) Ocain, T. D.; Rich, D. H. J. Med. Chem. 1992, 35, 451. (c) Yuan, W.; Munoz, B.; Wong, C.-H. J. Med. Chem. 1993, 36, 211. (d) Peet, N. P.; Burkhart, J. P.; Angelastro, M. R.; Giroux, E. L.; Mehdi, S.; Bey, P.; Kolb, M.; Neises, B.; Schiriin, D. J. Med. Chem. 1990, 33, 394. (e) Gelb, M. H.; Svaren, J. P.; Abeles, R. H. Biochemistry 1985, 24, 1813. (f) Parisi, M. F.; Abeles, R. H. Biochemistry 1992, 31, 9429.
27. The hydration of electrophilic ketones has been of recent interest, (a) Krois, D.; Langer, E.; Lehner, H. Tetrahedron 1980, 36, 1345. (b) Ocain, T. D.; Rich, D. H. J. Med. Chem. 1992, 35, 451. (c) Yuan, W.; Munoz, B.; Wong, C.-H. J. Med. Chem. 1993, 36, 211. (d) Peet, N. P.; Burkhart, J. P.; Angelastro, M. R.; Giroux, E. L.; Mehdi, S.; Bey, P.; Kolb, M.; Neises, B.; Schiriin, D. J. Med. Chem. 1990, 33, 394. (e) Gelb, M. H.; Svaren, J. P.; Abeles, R. H. Biochemistry 1985, 24, 1813. (f) Parisi, M. F.; Abeles, R. H. Biochemistry 1992, 31, 9429.
28. The hydration of electrophilic ketones has been of recent interest, (a) Krois, D.; Langer, E.; Lehner, H. Tetrahedron 1980, 36, 1345. (b) Ocain, T. D.; Rich, D. H. J. Med. Chem. 1992, 35, 451. (c) Yuan, W.; Munoz, B.; Wong, C.-H. J. Med. Chem. 1993, 36, 211. (d) Peet, N. P.; Burkhart, J. P.; Angelastro, M. R.; Giroux, E. L.; Mehdi, S.; Bey, P.; Kolb, M.; Neises, B.; Schiriin, D. J. Med. Chem. 1990, 33, 394. (e) Gelb, M. H.; Svaren, J. P.; Abeles, R. H. Biochemistry 1985, 24, 1813. (f) Parisi, M. F.; Abeles, R. H. Biochemistry 1992, 31, 9429.
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32. In the case of 7f, reduction product ii was isolated from the reaction mixture.
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34. For other examples of cis-trans assignments of glycidic esters by NMR see: (a) Akita, H.; Matsukura, H.; Oishi, T. Tetrahedron Lett. 1986, 27, 5397. (b) Petit, Y.; Sanner, C.; Larcheveque, M. Synthesis 1988, 538. (c) Abel-Magid, A.; Pridgen, L. N.; Eggleton, D. S.; Lantos, I. J. Am. Chem. Soc. 1986, 108, 4595. (d) Denis, J.-M.; Correa, A. Greene, A. E. J. Org. Chem. 1990, 55, 1957. (e) Denis, J.-M.; Greene, A. E.; Serra, A. A.; Luche, M.-J. J. Org. Chem. 1986, 51, 46, (f) Caldwell, C. G.; Bondy, S. S. Synthesis 1990, 34.
35. For other examples of cis-trans assignments of glycidic esters by NMR see: (a) Akita, H.; Matsukura, H.; Oishi, T. Tetrahedron Lett. 1986, 27, 5397. (b) Petit, Y.; Sanner, C.; Larcheveque, M. Synthesis 1988, 538. (c) Abel-Magid, A.; Pridgen, L. N.; Eggleton, D. S.; Lantos, I. J. Am. Chem. Soc. 1986, 108, 4595. (d) Denis, J.-M.; Correa, A. Greene, A. E. J. Org. Chem. 1990, 55, 1957. (e) Denis, J.-M.; Greene, A. E.; Serra, A. A.; Luche, M.-J. J. Org. Chem. 1986, 51, 46, (f) Caldwell, C. G.; Bondy, S. S. Synthesis 1990, 34.
36. For other examples of cis-trans assignments of glycidic esters by NMR see: (a) Akita, H.; Matsukura, H.; Oishi, T. Tetrahedron Lett. 1986, 27, 5397. (b) Petit, Y.; Sanner, C.; Larcheveque, M. Synthesis 1988, 538. (c) Abel-Magid, A.; Pridgen, L. N.; Eggleton, D. S.; Lantos, I. J. Am. Chem. Soc. 1986, 108, 4595. (d) Denis, J.-M.; Correa, A. Greene, A. E. J. Org. Chem. 1990, 55, 1957. (e) Denis, J.-M.; Greene, A. E.; Serra, A. A.; Luche, M.-J. J. Org. Chem. 1986, 51, 46, (f) Caldwell, C. G.; Bondy, S. S. Synthesis 1990, 34.
37. For other examples of cis-trans assignments of glycidic esters by NMR see: (a) Akita, H.; Matsukura, H.; Oishi, T. Tetrahedron Lett. 1986, 27, 5397. (b) Petit, Y.; Sanner, C.; Larcheveque, M. Synthesis 1988, 538. (c) Abel-Magid, A.; Pridgen, L. N.; Eggleton, D. S.; Lantos, I. J. Am. Chem. Soc. 1986, 108, 4595. (d) Denis, J.-M.; Correa, A. Greene, A. E. J. Org. Chem. 1990, 55, 1957. (e) Denis, J.-M.; Greene, A. E.; Serra, A. A.; Luche, M.-J. J. Org. Chem. 1986, 51, 46, (f) Caldwell, C. G.; Bondy, S. S. Synthesis 1990, 34.
38. For other examples of cis-trans assignments of glycidic esters by NMR see: (a) Akita, H.; Matsukura, H.; Oishi, T. Tetrahedron Lett. 1986, 27, 5397. (b) Petit, Y.; Sanner, C.; Larcheveque, M. Synthesis 1988, 538. (c) Abel-Magid, A.; Pridgen, L. N.; Eggleton, D. S.; Lantos, I. J. Am. Chem. Soc. 1986, 108, 4595. (d) Denis, J.-M.; Correa, A. Greene, A. E. J. Org. Chem. 1990, 55, 1957. (e) Denis, J.-M.; Greene, A. E.; Serra, A. A.; Luche, M.-J. J. Org. Chem. 1986, 51, 46, (f) Caldwell, C. G.; Bondy, S. S. Synthesis 1990, 34.
39. For other examples of cis-trans assignments of glycidic esters by NMR see: (a) Akita, H.; Matsukura, H.; Oishi, T. Tetrahedron Lett. 1986, 27, 5397. (b) Petit, Y.; Sanner, C.; Larcheveque, M. Synthesis 1988, 538. (c) Abel-Magid, A.; Pridgen, L. N.; Eggleton, D. S.; Lantos, I. J. Am. Chem. Soc. 1986, 108, 4595. (d) Denis, J.-M.; Correa, A. Greene, A. E. J. Org. Chem. 1990, 55, 1957. (e) Denis, J.-M.; Greene, A. E.; Serra, A. A.; Luche, M.-J. J. Org. Chem. 1986, 51, 46, (f) Caldwell, C. G.; Bondy, S. S. Synthesis 1990, 34.
40. 5
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