Productive asymmetric synthesis of all four diastereomers of 3-(trans-2-nitrocyclopropyl)alanine from glycine with (S)- or (R)-2-[(N-benzylprolyl)amino]benzophenone as a reusable chiral auxiliary

European Journal of Organic Chemistry

Volumn , Issue 5, 2003, Pages 869-877

  Larionov, Oleg V ^a   Savel'eva, Tatyana F ^b   Kochetkov, Konstantin A ^b   Ikonnokov, Nikolai S ^b   Kozhushkov, Sergei I ^a   Yufit, Dmitrii S ^c   Howard, Judith A K ^c   Khrustalev, Viktor N ^b   Belokon, Yuri N ^b   De Meijere, Armin ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

^b A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

^c DURHAM UNIVERSITY   (United Kingdom)

Author keywords

Amino acids; Asymmetric synthesis; Chiral auxiliaries; Nickel; Nitrocyclopropylalanine

Indexed keywords

1 (IODOMETHYL) 2 NITROCYCLOPROPANE; 2 [(N BENZYLPROLYL)AMINO]BENZOPHENONE; 3 (2 NITROCYCLOPROPYL)ALANINE; ALANINE DERIVATIVE; ALKYLATING AGENT; BENZOPHENONE DERIVATIVE; GLYCINE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHIRALITY; CRYSTAL STRUCTURE; CRYSTALLIZATION; DIASTEREOISOMER; DILUTION; ION EXCHANGE CHROMATOGRAPHY; PURIFICATION; REACTION ANALYSIS; SOLUBILITY; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037338374     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200390131     Document Type: Article

References (46)

1. [1a] J. Salaün, M. S. Baird, Curr. Med. Chem. 1995, 2, 511-542.
2. [1b] J. Salaün, Top. Curr. Chem. 2000, 207, 1-67.
3. [2a] N. Anders, H. Wolf, H. Zähner, E. Rössner, A. Zeeck, W. A. König, V. Sinnwell, Helv. Chim. Acta 1989, 72, 426-437.
4. [2b] E. Rössner, A. Zeeck, W. A. König, Angew. Chem. 1990, 102, 84-85; Angew. Chem. Int. Ed. Engl. 1990, 29, 64-65.
5. [2b] E. Rössner, A. Zeeck, W. A. König, Angew. Chem. 1990, 102, 84-85; Angew. Chem. Int. Ed. Engl. 1990, 29, 64-65.
6. A. Asai, A. Hasegawa, K. Ochiai, Y. Yamashita, T. Mizukami, J. Antibiotics 2000, 53, 81-83.
7. [4a] B. Geers, P. Alvermann, M. Brandl, S. I. Kozhushkov, K. Wagner-Gillen, A. Zeeck, A. de Meijere, Eur. J. Org. Chem., to be submitted.
8. [4b] B. Geers, Dissertation, Universität Göttingen, 1998.
9. [4c] M. Brandl, Dissertation, Universität Göttingen, 2000.
10. [4d] P. Alvermann, Dissertation, Universität Göttingen, 2001.
11. B. Zlatopolsky, forthcoming Dissertation, Universität Göttingen, 2003.
12. [6a] J. Zindel, A. Zeeck, W. A. König, A. de Meijere, Tetrahedron Lett. 1993, 34, 1917-1920.
13. [6b] J. Zindel, A. de Meijere, Synthesis 1994, 190-194.
14. [6c] J. Zindel, A. de Meijere, J. Org. Chem. 1995, 60, 2968-2973.
15. [6d] J. Zindel, Dissertation, Universität Göttingen, 1993.
16. M. Brandl, S. I. Kozhushkov, K. Loscha, O. V. Kokoreva, D. S. Yufit, J. A. K. Howard, A. de Meijere, Synlett 2000, 12, 1741-1744.
17. C. Cativiela, M. D. Diaz-de-Villegas, Tetrahedron: Asymmetry 2000, 11, 645-732.
18. [9a] M. Calmes, J. Daunis, Amino Acids 1999, 16, 215-250.
19. [9b] S. Bouifraden, C. Drouot, M. El Hadrami, F. Guenoun, L. Lecointe, N. Mai, M. Paris, C. Pothion, M. Sadoune, B. Sauvagnat, M. Amblard, J. L. Augagnac, M. Calmes, P. Chevallet, J. Daunis, C. Enjalbal, J. A. Fehrentz, F. Lamaty, J. P. Lavergne, R. Lazaro, V. Rolland, M. L. Roumestant, P. Viallefont, Y. Vidal, J. Martinez, Amino Acids 1999, 16, 345-379.
20. [9c] T. Abellan, R. Chinchilla, N. Galindo, G. Guillena, C. Najera, J. M. Sansano, Eur J. Org. Chem. 2000, 2689-2697.
21. [9d] M. J. O'Donnell, Aldrichim. Acta 2001, 34, 3-15, and references cited therein.
22. For recent applications of this methodology see: [10a] Yu. N. Belokon, K. A. Kochetkov, N. S. Ikonnikov, T. V. Strelkova, S. R. Harutyunyan, A. S. Saghiyan, Tetrahedron: Asymmetry 2001, 12, 481-485. [10b] A. S. Saghiyan, A. V. Geolchanyan, S. M. Djamgaryan, S. M. Vardapetyan, V. I. Tararov, N. A. Kuz'mina, N. S. Ikonnikov, Yu. N. Belokon, M. North, Russ. Chem. Bull. 2000, 49, 1460-1463. [10c] For a review on the chiral auxiliary see: Yu. N. Belokon, Janssen Chim. Acta 1992, 10, 4-12.
23. For recent applications of this methodology see: [10a] Yu. N. Belokon, K. A. Kochetkov, N. S. Ikonnikov, T. V. Strelkova, S. R. Harutyunyan, A. S. Saghiyan, Tetrahedron: Asymmetry 2001, 12, 481-485. [10b] A. S. Saghiyan, A. V. Geolchanyan, S. M. Djamgaryan, S. M. Vardapetyan, V. I. Tararov, N. A. Kuz'mina, N. S. Ikonnikov, Yu. N. Belokon, M. North, Russ. Chem. Bull. 2000, 49, 1460-1463. [10c] For a review on the chiral auxiliary see: Yu. N. Belokon, Janssen Chim. Acta 1992, 10, 4-12.
24. For recent applications of this methodology see: [10a] Yu. N. Belokon, K. A. Kochetkov, N. S. Ikonnikov, T. V. Strelkova, S. R. Harutyunyan, A. S. Saghiyan, Tetrahedron: Asymmetry 2001, 12, 481-485. [10b] A. S. Saghiyan, A. V. Geolchanyan, S. M. Djamgaryan, S. M. Vardapetyan, V. I. Tararov, N. A. Kuz'mina, N. S. Ikonnikov, Yu. N. Belokon, M. North, Russ. Chem. Bull. 2000, 49, 1460-1463. [10c] For a review on the chiral auxiliary see: Yu. N. Belokon, Janssen Chim. Acta 1992, 10, 4-12.
25. [11a] C. Cai, V. A. Soloshonok, V. J. Hruby, J. Org. Chem. 2001, 4, 1339-1350.
26. [11b] A. Debache, S. Collett, P. Bauchat, D. Danion, L. Euzenat, A. Hercouet, B. Carboni, Tetrahedron: Asymmetry 2001, 13, 761-764.
27. [11c] R. N. Krasikova, O. S. Fedorova, V. V. Zaitzev, I. K. Mosevich, O. F. Kuznetsova, G. Westera, S. A. Ametamey, P. A. Schubiger, M. Nader, J. Labelled Comp. Radiopharm. 2001, 44, 143-147.
28. [11d] V. A. Soloshonok, C. Cai, X. Tang, V. J. Hruby, Tetrahedron 2000, 56, 2577-2582.
29. [11e] X. Tang, V. A. Soloshonok, V. J. Hruby, Tetrahedron: Assymmetry 2000, 11, 2917-2925.
30. [11f] V. A. Soloshonok, C. Cai, V. J. Hruby, Angew. Chem. 2000, 12, 2256-2259; Angew. Chem. Int. Ed. 2000, 39, 2172-2175.
31. [11f] V. A. Soloshonok, C. Cai, V. J. Hruby, Angew. Chem. 2000, 12, 2256-2259; Angew. Chem. Int. Ed. 2000, 39, 2172-2175.
32. [11g] V. A. Soloshonok, C. Cai, V. J. Hruby, Tetrahedron: Asymmetry 1999, 10, 4265-4270.
33. [11h] R. N. Krasikova, O. S. Fedorova, I. K. Mosevich, O. F. Kuznetsova, M. V. Korsakov, S. M. Ametamey, P. A. Schubiger, J. Labelled Compd. Radiopharm. 1999, 1, 102-104.
34. [11i] S. Collet, P. Bauchat, R. Danion-Bougot, D. Danion, Tetrahedron: Asymmetry 1998, 9, 2121-2131.
35. [11j] B. B. De, N. R. Thomas, Tetrahedron: Asymmetry 1997, 8, 2687-2691.
36. [11k] V. A. Soloshonok, D. V. Avilov, V. P. Kukhar, Tetrahedron 1996, 52, 12433-12442.
37. [11l] C. W. G. Fishwick, J. M. Sanderson, J. B. C. Findlay, Tetrahedron Lett. 1994, 35, 4611-4614.
38. [11m] V. I. Losilkina, V. I. Sokolov, Dokl. Chem. (Engl. Transl.) 1991, 1-3, 243-245; V. I. Losilkina, V. I. Sokolov, Dokl. Akad. Nauk SSSR Ser. Khim. 1991, 2, 339-342.
39. [11m] V. I. Losilkina, V. I. Sokolov, Dokl. Chem. (Engl. Transl.) 1991, 1-3, 243-245; V. I. Losilkina, V. I. Sokolov, Dokl. Akad. Nauk SSSR Ser. Khim. 1991, 2, 339-342.
40. [11n] K. J. Fasth, B. Langstrom, Acta Chem. Scand. 1990, 44, 720-725.
41. L. F. Tietze, C. Schneider, A. Grote, Chem. Eur. J. 1996, 2, 139-148, and references cited therein.
42. E. J. Corey, S. G. Pyne, W. Su, Tetrahedron Lett. 1983, 24, 4883-4886.
43. Yu. N. Belokon', V. I. Tararov, V. I. Maleev, T. F. Savel'eva, M. G. Ryzhov, Tetrahedron: Asymmetry 1998, 9, 4249-4252.
44. These data have been deposited with the Cambridge Crystallographic Data Centre and can be obtained free of charge at www.ccdc.cam.ac.uk/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: (internat.) + 44-1223/336-033; E-mail: deposit@ccdc.cam.ac.uk].
45. S. V. Lindeman, T. V. Timofeeva, V. I. Maleyev, Yu. N. Belokon', M. G. Ryzhov, V. M. Belikov, Yu. T. Struchkov, Acta Crystallogr., Sect. C 1985, 41, 1290-1295.
46. F. Allen, J. P. S. Lommerse, V. J. Hoy, J. A. K. Howard, G. R. Desiraju, Acta Crystallogr., Sect. B 1996, 52, 734-745.