Carbocyclic α,β-diamino acids: Asymmetric Strecker synthesis of stereomeric 1,2-diaminocyclohexanecarboxylic acids

Tetrahedron Asymmetry

Volumn 13, Issue 20, 2002, Pages 2241-2249

  Pai Fondekar, Kamalesh P ^a   Volk, Franz J ^a   Khaliq uz Zaman, S M ^a   Bisel, Philippe ^a   Frahm, August W ^a  

^a UNIVERSITY OF FREIBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; CARBOXYLIC ACID DERIVATIVE; CYANIDE; CYCLOHEXANONE DERIVATIVE; IMINE; NITRILE; PHENETHYLAMINE; SOLVENT; SULFURIC ACID;

ANALYTIC METHOD; ARTICLE; ASYMMETRIC SYNTHESIS; CHIRALITY; CRYSTAL STRUCTURE; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; HYDROLYSIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; PRIORITY JOURNAL; STEREOCHEMISTRY; STEREOISOMERISM; STRECKER SYNTHESIS; TEMPERATURE; X RAY CRYSTALLOGRAPHY;

EID: 0037131664     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(02)00610-9     Document Type: Article

References (31)

1. For reviews see: (a) Seebach, D.; Hoffmann, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2708; (b) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225.
2. For reviews see: (a) Seebach, D.; Hoffmann, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2708; (b) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225.
3. For review, see: Kaul R., Balaram P. Bioorg. Med. Chem. 7:1999;105-117.
4. Shrader W.D., Marlowe C.K. Biorg. Med. Chem. Lett. 5:1995;2207.
5. Boyce R.J., Mulqueen G.C., Pattenden G. Tetrahedron. 51:1995;7321.
6. Breveglieri A., Guerrini R., Salvadori S., Bianchi C., Bryant S.D., Attila M., Lazarus L.H. J. Med. Chem. 39:1996;773.
7. Gershonov E., Granoth R., Tzehoval E., Gaoni Y., Fridkin M. J. Med. Chem. 39:1996;4833.
8. Horikawa M., Shigeri Y., Yumato N., Yoshikawa S., Nakaijima T., Ohfune Y. Bioorg. Med. Chem. Lett. 8:1998;2027.
9. Toth G.H., Bakos K., Penke B., Pavo I., Varga C., Torok G., Peter A., Fulop F. Bioorg. Med. Chem. Lett. 9:1999;667.
10. Bedingfield J.S., Kemp M.C., Jane D.E., Tse H.W., Roberts P.J., Watkins J.C. Br. J. Pharmacol. 116:1995;3323.
11. Pellicciari R., Luneia R., Costantino G., Marinozzi M., Natalini B., Jakobsen P., Kanstrup A., Lombardi G., Moroni F., Thomsen C. J. Med. Chem. 38:1995;3717.
12. Trist D.G. Pharm. Act. Helv. 74:2000;221.
13. Acher F., Tellier F., Azerad R., Brabet I., Fagni L., Pin J.-P. J. Med. Chem. 40:1997;3119.
14. Allen C.N., Omelchenko I., Ros S.M., Spencer P. Neuropharmacology. 34:1995;651.
15. For review, see: Gellman S.H. Acc. Chem. Res. 31:1998;173.
16. For reviews on Asymmetric Strecker Synthesis, see: (a) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225-227; (b) Duthaler, R. O. Tetrahedron 1994, 50, 1539-1650; (c) Williams, R. M. Synthesis of Optically Active α-Amino Acids, Vol. 7 of Organic Chemistry Series, Baldwin, J. E.; Magnus, P. D., Eds.; Pergamon Press: Oxford, 1989; Chapter 5, pp. 208-229. For recent work on Asymmetric Strecker Synthesis, see: (a) Byrne, J.; Chavarot, M.; Chavant, P.; Vallee, Y. Tetrahedron Lett. 2000, 41, 873-876; (b) Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762-766; (c) Ma, D.; Guozhi, T.; Zou, G. Tetrahedron Lett. 1999, 40, 9385; (d) Ma, D.; Guozhi, T.; Zou, G. Tetrahedron Lett. 1999, 40, 5753-5756; (e) Corey, E. J.; Grogan, M. Org. Lett. 1999, 1, 157-160; (f) Ma, D.; Tian, H.; Zou, G. J. Org. Chem. 1999, 64, 120-125; (g) Dominguez, C.; et al. Tetrahedron Lett. 1998, 39, 9305-9308; (h) Vergne, C.; Bouillon, J.-P.; Chastanet, J.; Bois-Choussy, M.; Zhu, J. Tetrahedron: Asymmetry 1998, 9, 3095-3103.
17. For reviews on Asymmetric Strecker Synthesis, see: (a) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225-227; (b) Duthaler, R. O. Tetrahedron 1994, 50, 1539-1650; (c) Williams, R. M. Synthesis of Optically Active α-Amino Acids, Vol. 7 of Organic Chemistry Series, Baldwin, J. E.; Magnus, P. D., Eds.; Pergamon Press: Oxford, 1989; Chapter 5, pp. 208-229. For recent work on Asymmetric Strecker Synthesis, see: (a) Byrne, J.; Chavarot, M.; Chavant, P.; Vallee, Y. Tetrahedron Lett. 2000, 41, 873-876; (b) Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762-766; (c) Ma, D.; Guozhi, T.; Zou, G. Tetrahedron Lett. 1999, 40, 9385; (d) Ma, D.; Guozhi, T.; Zou, G. Tetrahedron Lett. 1999, 40, 5753-5756; (e) Corey, E. J.; Grogan, M. Org. Lett. 1999, 1, 157-160; (f) Ma, D.; Tian, H.; Zou, G. J. Org. Chem. 1999, 64, 120-125; (g) Dominguez, C.; et al. Tetrahedron Lett. 1998, 39, 9305-9308; (h) Vergne, C.; Bouillon, J.-P.; Chastanet, J.; Bois-Choussy, M.; Zhu, J. Tetrahedron: Asymmetry 1998, 9, 3095-3103.
18. For reviews on Asymmetric Strecker Synthesis, see: (a) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225-227; (b) Duthaler, R. O. Tetrahedron 1994, 50, 1539-1650; (c) Williams, R. M. Synthesis of Optically Active α-Amino Acids, Vol. 7 of Organic Chemistry Series, Baldwin, J. E.; Magnus, P. D., Eds.; Pergamon Press: Oxford, 1989; Chapter 5, pp. 208-229. For recent work on Asymmetric Strecker Synthesis, see: (a) Byrne, J.; Chavarot, M.; Chavant, P.; Vallee, Y. Tetrahedron Lett. 2000, 41, 873-876; (b) Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762-766; (c) Ma, D.; Guozhi, T.; Zou, G. Tetrahedron Lett. 1999, 40, 9385; (d) Ma, D.; Guozhi, T.; Zou, G. Tetrahedron Lett. 1999, 40, 5753-5756; (e) Corey, E. J.; Grogan, M. Org. Lett. 1999, 1, 157-160; (f) Ma, D.; Tian, H.; Zou, G. J. Org. Chem. 1999, 64, 120-125; (g) Dominguez, C.; et al. Tetrahedron Lett. 1998, 39, 9305-9308; (h) Vergne, C.; Bouillon, J.-P.; Chastanet, J.; Bois-Choussy, M.; Zhu, J. Tetrahedron: Asymmetry 1998, 9, 3095-3103.
19. For reviews on Asymmetric Strecker Synthesis, see: (a) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225-227; (b) Duthaler, R. O. Tetrahedron 1994, 50, 1539-1650; (c) Williams, R. M. Synthesis of Optically Active α-Amino Acids, Vol. 7 of Organic Chemistry Series, Baldwin, J. E.; Magnus, P. D., Eds.; Pergamon Press: Oxford, 1989; Chapter 5, pp. 208-229. For recent work on Asymmetric Strecker Synthesis, see: (a) Byrne, J.; Chavarot, M.; Chavant, P.; Vallee, Y. Tetrahedron Lett. 2000, 41, 873-876; (b) Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762-766; (c) Ma, D.; Guozhi, T.; Zou, G. Tetrahedron Lett. 1999, 40, 9385; (d) Ma, D.; Guozhi, T.; Zou, G. Tetrahedron Lett. 1999, 40, 5753-5756; (e) Corey, E. J.; Grogan, M. Org. Lett. 1999, 1, 157-160; (f) Ma, D.; Tian, H.; Zou, G. J. Org. Chem. 1999, 64, 120-125; (g) Dominguez, C.; et al. Tetrahedron Lett. 1998, 39, 9305-9308; (h) Vergne, C.; Bouillon, J.-P.; Chastanet, J.; Bois-Choussy, M.; Zhu, J. Tetrahedron: Asymmetry 1998, 9, 3095-3103.
20. For reviews on Asymmetric Strecker Synthesis, see: (a) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225-227; (b) Duthaler, R. O. Tetrahedron 1994, 50, 1539-1650; (c) Williams, R. M. Synthesis of Optically Active α-Amino Acids, Vol. 7 of Organic Chemistry Series, Baldwin, J. E.; Magnus, P. D., Eds.; Pergamon Press: Oxford, 1989; Chapter 5, pp. 208-229. For recent work on Asymmetric Strecker Synthesis, see: (a) Byrne, J.; Chavarot, M.; Chavant, P.; Vallee, Y. Tetrahedron Lett. 2000, 41, 873-876; (b) Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762-766; (c) Ma, D.; Guozhi, T.; Zou, G. Tetrahedron Lett. 1999, 40, 9385; (d) Ma, D.; Guozhi, T.; Zou, G. Tetrahedron Lett. 1999, 40, 5753-5756; (e) Corey, E. J.; Grogan, M. Org. Lett. 1999, 1, 157-160; (f) Ma, D.; Tian, H.; Zou, G. J. Org. Chem. 1999, 64, 120-125; (g) Dominguez, C.; et al. Tetrahedron Lett. 1998, 39, 9305-9308; (h) Vergne, C.; Bouillon, J.-P.; Chastanet, J.; Bois-Choussy, M.; Zhu, J. Tetrahedron: Asymmetry 1998, 9, 3095-3103.
21. For reviews on Asymmetric Strecker Synthesis, see: (a) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225-227; (b) Duthaler, R. O. Tetrahedron 1994, 50, 1539-1650; (c) Williams, R. M. Synthesis of Optically Active α-Amino Acids, Vol. 7 of Organic Chemistry Series, Baldwin, J. E.; Magnus, P. D., Eds.; Pergamon Press: Oxford, 1989; Chapter 5, pp. 208-229. For recent work on Asymmetric Strecker Synthesis, see: (a) Byrne, J.; Chavarot, M.; Chavant, P.; Vallee, Y. Tetrahedron Lett. 2000, 41, 873-876; (b) Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762-766; (c) Ma, D.; Guozhi, T.; Zou, G. Tetrahedron Lett. 1999, 40, 9385; (d) Ma, D.; Guozhi, T.; Zou, G. Tetrahedron Lett. 1999, 40, 5753-5756; (e) Corey, E. J.; Grogan, M. Org. Lett. 1999, 1, 157-160; (f) Ma, D.; Tian, H.; Zou, G. J. Org. Chem. 1999, 64, 120-125; (g) Dominguez, C.; et al. Tetrahedron Lett. 1998, 39, 9305-9308; (h) Vergne, C.; Bouillon, J.-P.; Chastanet, J.; Bois-Choussy, M.; Zhu, J. Tetrahedron: Asymmetry 1998, 9, 3095-3103.
22. For reviews on Asymmetric Strecker Synthesis, see: (a) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225-227; (b) Duthaler, R. O. Tetrahedron 1994, 50, 1539-1650; (c) Williams, R. M. Synthesis of Optically Active α-Amino Acids, Vol. 7 of Organic Chemistry Series, Baldwin, J. E.; Magnus, P. D., Eds.; Pergamon Press: Oxford, 1989; Chapter 5, pp. 208-229. For recent work on Asymmetric Strecker Synthesis, see: (a) Byrne, J.; Chavarot, M.; Chavant, P.; Vallee, Y. Tetrahedron Lett. 2000, 41, 873-876; (b) Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762-766; (c) Ma, D.; Guozhi, T.; Zou, G. Tetrahedron Lett. 1999, 40, 9385; (d) Ma, D.; Guozhi, T.; Zou, G. Tetrahedron Lett. 1999, 40, 5753-5756; (e) Corey, E. J.; Grogan, M. Org. Lett. 1999, 1, 157-160; (f) Ma, D.; Tian, H.; Zou, G. J. Org. Chem. 1999, 64, 120-125; (g) Dominguez, C.; et al. Tetrahedron Lett. 1998, 39, 9305-9308; (h) Vergne, C.; Bouillon, J.-P.; Chastanet, J.; Bois-Choussy, M.; Zhu, J. Tetrahedron: Asymmetry 1998, 9, 3095-3103.
23. For reviews on Asymmetric Strecker Synthesis, see: (a) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225-227; (b) Duthaler, R. O. Tetrahedron 1994, 50, 1539-1650; (c) Williams, R. M. Synthesis of Optically Active α-Amino Acids, Vol. 7 of Organic Chemistry Series, Baldwin, J. E.; Magnus, P. D., Eds.; Pergamon Press: Oxford, 1989; Chapter 5, pp. 208-229. For recent work on Asymmetric Strecker Synthesis, see: (a) Byrne, J.; Chavarot, M.; Chavant, P.; Vallee, Y. Tetrahedron Lett. 2000, 41, 873-876; (b) Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762-766; (c) Ma, D.; Guozhi, T.; Zou, G. Tetrahedron Lett. 1999, 40, 9385; (d) Ma, D.; Guozhi, T.; Zou, G. Tetrahedron Lett. 1999, 40, 5753-5756; (e) Corey, E. J.; Grogan, M. Org. Lett. 1999, 1, 157-160; (f) Ma, D.; Tian, H.; Zou, G. J. Org. Chem. 1999, 64, 120-125; (g) Dominguez, C.; et al. Tetrahedron Lett. 1998, 39, 9305-9308; (h) Vergne, C.; Bouillon, J.-P.; Chastanet, J.; Bois-Choussy, M.; Zhu, J. Tetrahedron: Asymmetry 1998, 9, 3095-3103.
24. For reviews on Asymmetric Strecker Synthesis, see: (a) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225-227; (b) Duthaler, R. O. Tetrahedron 1994, 50, 1539-1650; (c) Williams, R. M. Synthesis of Optically Active α-Amino Acids, Vol. 7 of Organic Chemistry Series, Baldwin, J. E.; Magnus, P. D., Eds.; Pergamon Press: Oxford, 1989; Chapter 5, pp. 208-229. For recent work on Asymmetric Strecker Synthesis, see: (a) Byrne, J.; Chavarot, M.; Chavant, P.; Vallee, Y. Tetrahedron Lett. 2000, 41, 873-876; (b) Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762-766; (c) Ma, D.; Guozhi, T.; Zou, G. Tetrahedron Lett. 1999, 40, 9385; (d) Ma, D.; Guozhi, T.; Zou, G. Tetrahedron Lett. 1999, 40, 5753-5756; (e) Corey, E. J.; Grogan, M. Org. Lett. 1999, 1, 157-160; (f) Ma, D.; Tian, H.; Zou, G. J. Org. Chem. 1999, 64, 120-125; (g) Dominguez, C.; et al. Tetrahedron Lett. 1998, 39, 9305-9308; (h) Vergne, C.; Bouillon, J.-P.; Chastanet, J.; Bois-Choussy, M.; Zhu, J. Tetrahedron: Asymmetry 1998, 9, 3095-3103.
25. For reviews on Asymmetric Strecker Synthesis, see: (a) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225-227; (b) Duthaler, R. O. Tetrahedron 1994, 50, 1539-1650; (c) Williams, R. M. Synthesis of Optically Active α-Amino Acids, Vol. 7 of Organic Chemistry Series, Baldwin, J. E.; Magnus, P. D., Eds.; Pergamon Press: Oxford, 1989; Chapter 5, pp. 208-229. For recent work on Asymmetric Strecker Synthesis, see: (a) Byrne, J.; Chavarot, M.; Chavant, P.; Vallee, Y. Tetrahedron Lett. 2000, 41, 873-876; (b) Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762-766; (c) Ma, D.; Guozhi, T.; Zou, G. Tetrahedron Lett. 1999, 40, 9385; (d) Ma, D.; Guozhi, T.; Zou, G. Tetrahedron Lett. 1999, 40, 5753-5756; (e) Corey, E. J.; Grogan, M. Org. Lett. 1999, 1, 157-160; (f) Ma, D.; Tian, H.; Zou, G. J. Org. Chem. 1999, 64, 120-125; (g) Dominguez, C.; et al. Tetrahedron Lett. 1998, 39, 9305-9308; (h) Vergne, C.; Bouillon, J.-P.; Chastanet, J.; Bois-Choussy, M.; Zhu, J. Tetrahedron: Asymmetry 1998, 9, 3095-3103.
26. For reviews on Asymmetric Strecker Synthesis, see: (a) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225-227; (b) Duthaler, R. O. Tetrahedron 1994, 50, 1539-1650; (c) Williams, R. M. Synthesis of Optically Active α-Amino Acids, Vol. 7 of Organic Chemistry Series, Baldwin, J. E.; Magnus, P. D., Eds.; Pergamon Press: Oxford, 1989; Chapter 5, pp. 208-229. For recent work on Asymmetric Strecker Synthesis, see: (a) Byrne, J.; Chavarot, M.; Chavant, P.; Vallee, Y. Tetrahedron Lett. 2000, 41, 873-876; (b) Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762-766; (c) Ma, D.; Guozhi, T.; Zou, G. Tetrahedron Lett. 1999, 40, 9385; (d) Ma, D.; Guozhi, T.; Zou, G. Tetrahedron Lett. 1999, 40, 5753-5756; (e) Corey, E. J.; Grogan, M. Org. Lett. 1999, 1, 157-160; (f) Ma, D.; Tian, H.; Zou, G. J. Org. Chem. 1999, 64, 120-125; (g) Dominguez, C.; et al. Tetrahedron Lett. 1998, 39, 9305-9308; (h) Vergne, C.; Bouillon, J.-P.; Chastanet, J.; Bois-Choussy, M.; Zhu, J. Tetrahedron: Asymmetry 1998, 9, 3095-3103.
27. Volk F.J., Frahm A.W. Liebigs Ann. Chem. 1996;1893.
28. Pai Fondekar K.P., Volk F.J., Frahm A.W. Tetrahedron: Asymmetry. 10:1999;727.
29. Wede J., Volk F.-J., Frahm A.W. Tetrahedron: Asymmetry. 11:2000;3231-3252.
30. Schlichter W.H., Frahm A.W. Arch. Pharm. 1993;429.
31. Schlauch M., Volk F.-J., Pai Fondekar K.P., Wede J., Frahm A.W. J. Chromatogr. A. 897:2000;145-152.