Enantioselective synthesis of (3R)- and (3S)-piperazic acids. The comparative unimportance of DMPU mediated retro-hydrazination

Tetrahedron

Volumn 52, Issue 3, 1996, Pages 1047-1068

  Hale, Karl J ^a   Cai, Jiaqiang ^a   Delisser, Vern ^a   Manaviazar, Soraya ^a   Peak, S Andrew ^a   Bhatia, Gurpreet S ^a   Collins, Timothy C ^a   Jogiya, Neha ^a  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

PIPERAZIC ACID; PIPERAZIC ACID DERIVATIVE; PIPERAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030025106     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)00938-8     Document Type: Article

References (42)

1. Bevan, K.; Davies, J.S.; Hassall, C.H.; Morton, R.B.; Phillips, D.A.S., J. Chem. Soc. (C), 1971, 514; Hassall, C.H.; Ogihara, Y.; Thomas, W.A., J. Chem. Soc. (C), 1971, 522.
2. Bevan, K.; Davies, J.S.; Hassall, C.H.; Morton, R.B.; Phillips, D.A.S., J. Chem. Soc. (C), 1971, 514; Hassall, C.H.; Ogihara, Y.; Thomas, W.A., J. Chem. Soc. (C), 1971, 522.
3. Azinothricin: Maehr, H.; Liu, C.-M.; Palleroni, N.J.; Smallheer, J.; Todaro, L.; Williams, T.H.; Blount, J.F., J. Antibiotics, 1986, 39, 17; A83586C: Smitka, T.A.; Deeter, J.B.; Hunt, A.H.; Mertz, F.P.; Ellis, R.M.; Boeck, L.D.; Yao, R.C., J. Antibiotics, 1988, 41, 726; Citropeptin: Nakagawa, M.; Hayakawa, Y.; Furihata, K.; Seto, H., J. Antibiotics, 1990, 43, 477; Hayakawa, Y.; Nakagawa, M.; Toda, Y.; Seto, H., Agric. Biol. Chem., 1990, 54, 1007.
4. Azinothricin: Maehr, H.; Liu, C.-M.; Palleroni, N.J.; Smallheer, J.; Todaro, L.; Williams, T.H.; Blount, J.F., J. Antibiotics, 1986, 39, 17; A83586C: Smitka, T.A.; Deeter, J.B.; Hunt, A.H.; Mertz, F.P.; Ellis, R.M.; Boeck, L.D.; Yao, R.C., J. Antibiotics, 1988, 41, 726; Citropeptin: Nakagawa, M.; Hayakawa, Y.; Furihata, K.; Seto, H., J. Antibiotics, 1990, 43, 477; Hayakawa, Y.; Nakagawa, M.; Toda, Y.; Seto, H., Agric. Biol. Chem., 1990, 54, 1007.
5. Azinothricin: Maehr, H.; Liu, C.-M.; Palleroni, N.J.; Smallheer, J.; Todaro, L.; Williams, T.H.; Blount, J.F., J. Antibiotics, 1986, 39, 17; A83586C: Smitka, T.A.; Deeter, J.B.; Hunt, A.H.; Mertz, F.P.; Ellis, R.M.; Boeck, L.D.; Yao, R.C., J. Antibiotics, 1988, 41, 726; Citropeptin: Nakagawa, M.; Hayakawa, Y.; Furihata, K.; Seto, H., J. Antibiotics, 1990, 43, 477; Hayakawa, Y.; Nakagawa, M.; Toda, Y.; Seto, H., Agric. Biol. Chem., 1990, 54, 1007.
6. Azinothricin: Maehr, H.; Liu, C.-M.; Palleroni, N.J.; Smallheer, J.; Todaro, L.; Williams, T.H.; Blount, J.F., J. Antibiotics, 1986, 39, 17; A83586C: Smitka, T.A.; Deeter, J.B.; Hunt, A.H.; Mertz, F.P.; Ellis, R.M.; Boeck, L.D.; Yao, R.C., J. Antibiotics, 1988, 41, 726; Citropeptin: Nakagawa, M.; Hayakawa, Y.; Furihata, K.; Seto, H., J. Antibiotics, 1990, 43, 477; Hayakawa, Y.; Nakagawa, M.; Toda, Y.; Seto, H., Agric. Biol. Chem., 1990, 54, 1007.
7. Suguwara, K.; Toda, S.; Moriyama, T.; Konishi, M.; Oki, T., J. Antibiotics, 1993, 46, 928.
8. Grafe, U.; Schlegel, R.; Ritzau, M.; Ihn, W.; Dornberger, K.; Stengel, C.; Fleck, W.F.; Gutsche, W.; Hartle, A., J. Antibiotics, 1995, 48, 119.
9. Hensens, O.D.; Borris, R.P.; Koupal, L.R.; Caldwell, C.G.; Currie, S.A.; Haidri, A.A.; Homnick, C.F.; Honeycutt, S.S.; Lindenmayer, S.M.; Schwartz, C.D.; Weissberger, B.A.; Woodruff, H.B.; Zink, D.L.; Zitano, L.; Fieldhouse, J.M.; Rollins, T.; Springer, M.S.; Springer, J.P., J. Antibiotics, 1991, 44, 249.
10. Ueno, M.; Amemiya, M.; Someno, T.; Masuda, T.; Iinuma, H.; Naganawa, H.; Hamada, M.; Ishizuka, M.; Takeuchi, T., J. Antibiotics, 1993, 46, 1658.
11. Pettibone, D.J.; Clineschmidt, B.V.; Anderson, P.S.; Freidinger, R.M.; Lundell, G.F.; Koupal, L.R.; Schwartz, C.D.; Williamson, J.M.; Goetz, M.A.; Hensens, O.D.; Liesch, J.M.; Springer, J.P., Endocrinology, 1989, 125, 217.
12. Ogita, T.; Sato, A.; Enokita, R.; Suzuki, K.; Ishii, M.; Negishi, T.; Okazaki, T.; Tamaki, K.; Tanzawa, K., J. Antibiotics, 1992, 45, 1723; Tamaki, T.; Ogita, T.; Tanzawa, K.; Sugimura, Y., Tetrahedron Lett., 1993, 34, 683; Tamaki, K.; Kurihara, S.; Sugimura, Y. Tetrahedron Lett., 1993, 34, 8477.
13. Ogita, T.; Sato, A.; Enokita, R.; Suzuki, K.; Ishii, M.; Negishi, T.; Okazaki, T.; Tamaki, K.; Tanzawa, K., J. Antibiotics, 1992, 45, 1723; Tamaki, T.; Ogita, T.; Tanzawa, K.; Sugimura, Y., Tetrahedron Lett., 1993, 34, 683; Tamaki, K.; Kurihara, S.; Sugimura, Y. Tetrahedron Lett., 1993, 34, 8477.
14. Ogita, T.; Sato, A.; Enokita, R.; Suzuki, K.; Ishii, M.; Negishi, T.; Okazaki, T.; Tamaki, K.; Tanzawa, K., J. Antibiotics, 1992, 45, 1723; Tamaki, T.; Ogita, T.; Tanzawa, K.; Sugimura, Y., Tetrahedron Lett., 1993, 34, 683; Tamaki, K.; Kurihara, S.; Sugimura, Y. Tetrahedron Lett., 1993, 34, 8477.
15. Attwood, M.R.; Francis, R.J.; Hassall, C.H.; Krohn, A.; Lawton, G.; Natoff, I.L.; Nixon, J.S.; Redshaw, S.; Thomas, W.A., FEBS Lett., 1984, 165, 201;
16. Attwood, M.R.; Hassall, C.H.; Krohn, A.; Lawton, G.; Redshaw, S., J. Chem. Soc. Perkin Trans. 1, 1986, 1011.
17. Johnston, G.A.R.; Stephanson, A.L.; Twitchin, B., J. Pharm. Pharmacol., 1977, 29, 240.
18. Hale, K.J.; Bhatia, G.S.; Peak, S.A.; Manaviazar, S., Tetrahedron Lett., 1993, 34, 5343; Hale, K.J.; Delisser, V.M.; Yeh, L.-K.; Peak, S.A.; Manaviazar, S.; Bhatia, G.S., Tetrahedron Lett., 1994, 35, 7685; Hale, K.J.; Cai, J.; Manaviazar, S.; Peak, S.A., Tetrahedron Lett., 1995, 36, 6965.
19. Hale, K.J.; Bhatia, G.S.; Peak, S.A.; Manaviazar, S., Tetrahedron Lett., 1993, 34, 5343; Hale, K.J.; Delisser, V.M.; Yeh, L.-K.; Peak, S.A.; Manaviazar, S.; Bhatia, G.S., Tetrahedron Lett., 1994, 35, 7685; Hale, K.J.; Cai, J.; Manaviazar, S.; Peak, S.A., Tetrahedron Lett., 1995, 36, 6965.
20. Hale, K.J.; Bhatia, G.S.; Peak, S.A.; Manaviazar, S., Tetrahedron Lett., 1993, 34, 5343; Hale, K.J.; Delisser, V.M.; Yeh, L.-K.; Peak, S.A.; Manaviazar, S.; Bhatia, G.S., Tetrahedron Lett., 1994, 35, 7685; Hale, K.J.; Cai, J.; Manaviazar, S.; Peak, S.A., Tetrahedron Lett., 1995, 36, 6965.
21. Hale, K.J.; Delisser, V.M.; Manaviazar, S., Tetrahedron Lett., 1992, 33, 7613; Hale, K.J., Patent Application No. PCT/GB93/02327; (this patent application has recently been relinquished by UCL so that any commercial organisation is now free to use our method without having to pay a royalty).
22. Hale, K.J.; Delisser, V.M.; Manaviazar, S., Tetrahedron Lett., 1992, 33, 7613; Hale, K.J., Patent Application No. PCT/GB93/02327; (this patent application has recently been relinquished by UCL so that any commercial organisation is now free to use our method without having to pay a royalty).
23. th ACS Meeting, Chicago, 1995, Abstract 205.
24. th ACS Meeting, Chicago, 1995, Abstract 205.
25. Evans, D.A.; Britton, T.C.; Dorow, R.L.; Dellaria, J.F., J. Am. Chem. Soc., 1986, 108, 6395; Evans, D.A.; Britton, T.C.; Dorow, R.L.; Dellaria, J.F., Tetrahedron, 1988, 44, 5525.
26. Evans, D.A.; Britton, T.C.; Dorow, R.L.; Dellaria, J.F., J. Am. Chem. Soc., 1986, 108, 6395; Evans, D.A.; Britton, T.C.; Dorow, R.L.; Dellaria, J.F., Tetrahedron, 1988, 44, 5525.
27. Trimble, L.A.; Vederas, J.C., J. Am. Chem. Soc., 1986, 108, 6397.
28. It is not essential to use 26 eq. of DMPU in this experiment; 16.5 eq of DMPU gives identical results.
29. th ACS Meeting, Miami Beach, 1989, Abstracts 118 and 119.
30. th ACS Meeting, Miami Beach, 1989, Abstracts 118 and 119.
31. Nakamura, Y.; Ito, A.; Shin, C., Bull. Chem. Soc. Jpn, 1994, 67, 2151; Nakamura, Y.; Shin, C., Chem. Lett., 1991, 1953.
32. Nakamura, Y.; Ito, A.; Shin, C., Bull. Chem. Soc. Jpn, 1994, 67, 2151; Nakamura, Y.; Shin, C., Chem. Lett., 1991, 1953.
33. Evans, D.A.; Ennis, M.O.; Mathre, D.J., J. Am. Chem. Soc., 1982, 104, 1737.
34. For alternative synthetic strategies to piperazic acid derivatives see: (a) Hassall, C.H.; Johnson, W.H.; Theobald, C.J., J. Chem. Soc. Perkin Trans.1, 1979, 1451;
35. (b) Adams, C.E.; Aguilar, D.; Hertel, S.; Knight, W.H.; Paterson, J., Synth. Comm., 1988, 18, 2225;
36. Hughes, P.; Clardy, J., J. Org. Chem., 1989, 54, 3260;
37. Aspinall, I.H.; Cowley, P.M.; Mitchell, G.; Stoodley, R.J., J. Chem. Soc. Chem. Commun., 1993, 1179;
38. (e) Schmidt, U.; Riedl, B., Synthesis, 1993, 809;
39. (f) Rutjes, F.P.J.T.; Teerhuis, N.M.; Hiemstra, H.; Speckamp, W.N., Tetrahedron, 1993, 49, 8605;
40. (g) Ciufolini, M.A.; Xi, N., J. Chem. Soc. Chem. Commun., 1994, 1867;
41. (h) see also Ref.18.
42. 2 was added to the remaining residue, and the -78 °C solution cannulated into the reaction mixture.