Stereocontrolled Synthesis of syn and anti N-Protected 3- Amino-2-Hydroxy Alkanoic Esters from Aminoalkyl Epoxides

Synlett

Volumn 1996, Issue 6, 1996, Pages 585-586

  Pegorier L ^a   Haddad, M ^a   Larcheveque M ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0343844564     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5487     Document Type: Article

References (36)

1. Guénard, F.; Guéritte-Voegelin, F.; Potier, P. Acc. Chem. Res. 1993, 26, 160.
2. Aoyagi, T.; Tobe, H.; Suda, H.; Hamada, M.; Takeucje, T.; Umezawa, H. J. Antibiot. 1976, 29, 97 and 100.
3. Szelke, M.; Leckie, B.; Hallett, A.; Jones, D.M.; Sveiras, J.; Atrash, B.; Lever, A.F. Nature 1982, 299, 555; Holladay, M.W.; Rich, D. Tetrahedron Lett. 1983, 24, 4401; Tam, T.F.; Carrière, J.; MacDonald, D.; Castelhano, A.L.; Pliura, D.H.; Dewdney, N.J.; Thomas, E.M.; Bach, C.; Barnett, J.; Chan, H.; Krantz, A. J. Med. Chem. 1992, 35, 1318; Mimoto, T.; Imai, J.; Kisanuki, S.; Enomoto, H.; Hattori, N.; Akaji, K.; Kiso, Y. Chem. Pharm. Bull. 1992, 40, 2251.
4. Szelke, M.; Leckie, B.; Hallett, A.; Jones, D.M.; Sveiras, J.; Atrash, B.; Lever, A.F. Nature 1982, 299, 555; Holladay, M.W.; Rich, D. Tetrahedron Lett. 1983, 24, 4401; Tam, T.F.; Carrière, J.; MacDonald, D.; Castelhano, A.L.; Pliura, D.H.; Dewdney, N.J.; Thomas, E.M.; Bach, C.; Barnett, J.; Chan, H.; Krantz, A. J. Med. Chem. 1992, 35, 1318; Mimoto, T.; Imai, J.; Kisanuki, S.; Enomoto, H.; Hattori, N.; Akaji, K.; Kiso, Y. Chem. Pharm. Bull. 1992, 40, 2251.
5. Szelke, M.; Leckie, B.; Hallett, A.; Jones, D.M.; Sveiras, J.; Atrash, B.; Lever, A.F. Nature 1982, 299, 555; Holladay, M.W.; Rich, D. Tetrahedron Lett. 1983, 24, 4401; Tam, T.F.; Carrière, J.; MacDonald, D.; Castelhano, A.L.; Pliura, D.H.; Dewdney, N.J.; Thomas, E.M.; Bach, C.; Barnett, J.; Chan, H.; Krantz, A. J. Med. Chem. 1992, 35, 1318; Mimoto, T.; Imai, J.; Kisanuki, S.; Enomoto, H.; Hattori, N.; Akaji, K.; Kiso, Y. Chem. Pharm. Bull. 1992, 40, 2251.
6. Szelke, M.; Leckie, B.; Hallett, A.; Jones, D.M.; Sveiras, J.; Atrash, B.; Lever, A.F. Nature 1982, 299, 555; Holladay, M.W.; Rich, D. Tetrahedron Lett. 1983, 24, 4401; Tam, T.F.; Carrière, J.; MacDonald, D.; Castelhano, A.L.; Pliura, D.H.; Dewdney, N.J.; Thomas, E.M.; Bach, C.; Barnett, J.; Chan, H.; Krantz, A. J. Med. Chem. 1992, 35, 1318; Mimoto, T.; Imai, J.; Kisanuki, S.; Enomoto, H.; Hattori, N.; Akaji, K.; Kiso, Y. Chem. Pharm. Bull. 1992, 40, 2251.
7. Izuka, K.; Kamijo, T.; Harada, H.; Akahane, T.; Kubota, T.; Umayama, H.; Kiso, Y. J. Chem. Soc., Chem. Commun. 1989, 1678; Okino, T.; Matsuda, H.; Murakami, M.; Yamaguchi, K. Tetrahedron Lett. 1993, 34, 501.
8. Izuka, K.; Kamijo, T.; Harada, H.; Akahane, T.; Kubota, T.; Umayama, H.; Kiso, Y. J. Chem. Soc., Chem. Commun. 1989, 1678; Okino, T.; Matsuda, H.; Murakami, M.; Yamaguchi, K. Tetrahedron Lett. 1993, 34, 501.
9. Melon, D.; Gravier-Pelletier, C.; LeMerrer, Y.; Depezay, J.C. Bull. Soc. Chim. Fr. 1992, 129, 585; Hattari, K. Miyata, M.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 1151; Kise, N.; Inakoshi, N.; Matsumara, Y. Tetrahedron Lett. 1995, 36, 909.
10. Melon, D.; Gravier-Pelletier, C.; LeMerrer, Y.; Depezay, J.C. Bull. Soc. Chim. Fr. 1992, 129, 585; Hattari, K. Miyata, M.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 1151; Kise, N.; Inakoshi, N.; Matsumara, Y. Tetrahedron Lett. 1995, 36, 909.
11. Melon, D.; Gravier-Pelletier, C.; LeMerrer, Y.; Depezay, J.C. Bull. Soc. Chim. Fr. 1992, 129, 585; Hattari, K. Miyata, M.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 1151; Kise, N.; Inakoshi, N.; Matsumara, Y. Tetrahedron Lett. 1995, 36, 909.
12. Pearson, W.H.; Hines, J.V. J. Org. Chem. 1989, 54, 4235; Herranz, R.; Castro-Pichel, J.; Vinuesa, S.; Garcia-Lopez, M.T. J. Org. Chem. 1990, 55, 2232; Ojima, I.; Park, Y.H.; Sun, C.M.; Brigaud, T.; Zhao, M. Tetrahedron Lett. 1992, 33, 5737; Jefford, C.W.; Wang, J.B.; Lu, Z.H. Tetrahedron Lett. 1993, 34, 7557; Hormuth, S.; Reibig, H.U.; Dorsch, D. Liebigs Ann. Chem. 1994, 121. For syntheses of the anti isomers, see: Bunnage, M.E.; Davies, S.G.; Goodwin, C.J. Synlett, 1993, 731; Pasto, M.; Moyano, A.; Pericas, M.A.; Riera, A. Tetrahedron : Asymmetry 1995, 6, 2329.
13. Pearson, W.H.; Hines, J.V. J. Org. Chem. 1989, 54, 4235; Herranz, R.; Castro-Pichel, J.; Vinuesa, S.; Garcia-Lopez, M.T. J. Org. Chem. 1990, 55, 2232; Ojima, I.; Park, Y.H.; Sun, C.M.; Brigaud, T.; Zhao, M. Tetrahedron Lett. 1992, 33, 5737; Jefford, C.W.; Wang, J.B.; Lu, Z.H. Tetrahedron Lett. 1993, 34, 7557; Hormuth, S.; Reibig, H.U.; Dorsch, D. Liebigs Ann. Chem. 1994, 121. For syntheses of the anti isomers, see: Bunnage, M.E.; Davies, S.G.; Goodwin, C.J. Synlett, 1993, 731; Pasto, M.; Moyano, A.; Pericas, M.A.; Riera, A. Tetrahedron : Asymmetry 1995, 6, 2329.
14. Pearson, W.H.; Hines, J.V. J. Org. Chem. 1989, 54, 4235; Herranz, R.; Castro-Pichel, J.; Vinuesa, S.; Garcia-Lopez, M.T. J. Org. Chem. 1990, 55, 2232; Ojima, I.; Park, Y.H.; Sun, C.M.; Brigaud, T.; Zhao, M. Tetrahedron Lett. 1992, 33, 5737; Jefford, C.W.; Wang, J.B.; Lu, Z.H. Tetrahedron Lett. 1993, 34, 7557; Hormuth, S.; Reibig, H.U.; Dorsch, D. Liebigs Ann. Chem. 1994, 121. For syntheses of the anti isomers, see: Bunnage, M.E.; Davies, S.G.; Goodwin, C.J. Synlett, 1993, 731; Pasto, M.; Moyano, A.; Pericas, M.A.; Riera, A. Tetrahedron : Asymmetry 1995, 6, 2329.
15. Pearson, W.H.; Hines, J.V. J. Org. Chem. 1989, 54, 4235; Herranz, R.; Castro-Pichel, J.; Vinuesa, S.; Garcia-Lopez, M.T. J. Org. Chem. 1990, 55, 2232; Ojima, I.; Park, Y.H.; Sun, C.M.; Brigaud, T.; Zhao, M. Tetrahedron Lett. 1992, 33, 5737; Jefford, C.W.; Wang, J.B.; Lu, Z.H. Tetrahedron Lett. 1993, 34, 7557; Hormuth, S.; Reibig, H.U.; Dorsch, D. Liebigs Ann. Chem. 1994, 121. For syntheses of the anti isomers, see: Bunnage, M.E.; Davies, S.G.; Goodwin, C.J. Synlett, 1993, 731; Pasto, M.; Moyano, A.; Pericas, M.A.; Riera, A. Tetrahedron : Asymmetry 1995, 6, 2329.
16. Pearson, W.H.; Hines, J.V. J. Org. Chem. 1989, 54, 4235; Herranz, R.; Castro-Pichel, J.; Vinuesa, S.; Garcia-Lopez, M.T. J. Org. Chem. 1990, 55, 2232; Ojima, I.; Park, Y.H.; Sun, C.M.; Brigaud, T.; Zhao, M. Tetrahedron Lett. 1992, 33, 5737; Jefford, C.W.; Wang, J.B.; Lu, Z.H. Tetrahedron Lett. 1993, 34, 7557; Hormuth, S.; Reibig, H.U.; Dorsch, D. Liebigs Ann. Chem. 1994, 121. For syntheses of the anti isomers, see: Bunnage, M.E.; Davies, S.G.; Goodwin, C.J. Synlett, 1993, 731; Pasto, M.; Moyano, A.; Pericas, M.A.; Riera, A. Tetrahedron : Asymmetry 1995, 6, 2329.
17. Pearson, W.H.; Hines, J.V. J. Org. Chem. 1989, 54, 4235; Herranz, R.; Castro-Pichel, J.; Vinuesa, S.; Garcia-Lopez, M.T. J. Org. Chem. 1990, 55, 2232; Ojima, I.; Park, Y.H.; Sun, C.M.; Brigaud, T.; Zhao, M. Tetrahedron Lett. 1992, 33, 5737; Jefford, C.W.; Wang, J.B.; Lu, Z.H. Tetrahedron Lett. 1993, 34, 7557; Hormuth, S.; Reibig, H.U.; Dorsch, D. Liebigs Ann. Chem. 1994, 121. For syntheses of the anti isomers, see: Bunnage, M.E.; Davies, S.G.; Goodwin, C.J. Synlett, 1993, 731; Pasto, M.; Moyano, A.; Pericas, M.A.; Riera, A. Tetrahedron : Asymmetry 1995, 6, 2329.
18. Pearson, W.H.; Hines, J.V. J. Org. Chem. 1989, 54, 4235; Herranz, R.; Castro-Pichel, J.; Vinuesa, S.; Garcia-Lopez, M.T. J. Org. Chem. 1990, 55, 2232; Ojima, I.; Park, Y.H.; Sun, C.M.; Brigaud, T.; Zhao, M. Tetrahedron Lett. 1992, 33, 5737; Jefford, C.W.; Wang, J.B.; Lu, Z.H. Tetrahedron Lett. 1993, 34, 7557; Hormuth, S.; Reibig, H.U.; Dorsch, D. Liebigs Ann. Chem. 1994, 121. For syntheses of the anti isomers, see: Bunnage, M.E.; Davies, S.G.; Goodwin, C.J. Synlett, 1993, 731; Pasto, M.; Moyano, A.; Pericas, M.A.; Riera, A. Tetrahedron : Asymmetry 1995, 6, 2329.
19. Ishibuchi, S.; Nagatani, T.; Ishizuka, T.; Kunieda, T. Nat. Prod. Lett. 1992, 1, 21;
20. Pégorier, L.; Petit, Y.; Larchevêque, M. J. Chem. Soc., Chem. Commun. 1994, 633; Pégorier, L. Petit, Y.; Mambu, A.; Larchevêque, M. Synthesis, 1994, 1403.
21. Pégorier, L.; Petit, Y.; Larchevêque, M. J. Chem. Soc., Chem. Commun. 1994, 633; Pégorier, L. Petit, Y.; Mambu, A.; Larchevêque, M. Synthesis, 1994, 1403.
22. Cardillo, G.; Orena, M.; Sandri, S.; Tomasini, C. Tetrahedron 1985, 41, 163.
23. 2- form) (2g, 3meq/g) was added and the mixture was stirred for 48h at 20°C. After filtration and evaporation, the crude product was chromatographed on silica gel.
24. 4,5 trans): Foglia, T.A.; Swern, D. J. Org. Chem. 1969, 34, 1680.
25. McDonald, C.E.; Nice, L.E.; Shaw, A.W.; Nestor, N.B. Tetrahedron Lett. 1993, 34, 2741.
26. Carlsen, P.H.J.; Katsuki, T.; Martin, V.S.; Sharpless, K.B. J. Org. Chem. 1981, 46, 3936.
27. Brook, M.A.; Chan, T.H. Synthesis, 1983, 201.
28. Ishizuka, T.; Kunieda, T. Tetrahedron Lett. 1987, 28, 4185.
29. 3).
30. For recent reports concerning the opening of epoxides by O-nucleophiles, see: Caron, M.; Sharpless, K.B. J. Org. Chem. 1985, 50, 1557; Guivisdalsky, P.N.; Bittman, R. J. Am. Chem. Soc. 1989, 111, 3077; Chini, M.; Crotti, P.; Gardelli, C.; Macchia, F. Synlett 1992, 673; Masaki, Y.; Miura, T.; Ochiai, M. Synlett 1993, 847.
31. For recent reports concerning the opening of epoxides by O-nucleophiles, see: Caron, M.; Sharpless, K.B. J. Org. Chem. 1985, 50, 1557; Guivisdalsky, P.N.; Bittman, R. J. Am. Chem. Soc. 1989, 111, 3077; Chini, M.; Crotti, P.; Gardelli, C.; Macchia, F. Synlett 1992, 673; Masaki, Y.; Miura, T.; Ochiai, M. Synlett 1993, 847.
32. For recent reports concerning the opening of epoxides by O-nucleophiles, see: Caron, M.; Sharpless, K.B. J. Org. Chem. 1985, 50, 1557; Guivisdalsky, P.N.; Bittman, R. J. Am. Chem. Soc. 1989, 111, 3077; Chini, M.; Crotti, P.; Gardelli, C.; Macchia, F. Synlett 1992, 673; Masaki, Y.; Miura, T.; Ochiai, M. Synlett 1993, 847.
33. For recent reports concerning the opening of epoxides by O-nucleophiles, see: Caron, M.; Sharpless, K.B. J. Org. Chem. 1985, 50, 1557; Guivisdalsky, P.N.; Bittman, R. J. Am. Chem. Soc. 1989, 111, 3077; Chini, M.; Crotti, P.; Gardelli, C.; Macchia, F. Synlett 1992, 673; Masaki, Y.; Miura, T.; Ochiai, M. Synlett 1993, 847.
34. Experimental: N-benzylated epoxyamine (3 mmol) was added to a suspension of cupric acetate (6mmol) and lithium acetate (3 mmol) in DMF (25 ml) and stirred for 24h at 50°C. After work-up, the mixture was extracted and purified by liquid chromatography on silica gel.
35. Sakaitani, M.; Hori, K.; Ohfune, Y. Tetrahedron Lett. 1988, 29, 2983.
36. 2)