Electrochemical oxidation of chiral 5-substituted 2-oxazolidinones: A key building block for dichiral β-amino alcohols

Tetrahedron

Volumn 52, Issue 29, 1996, Pages 9743-9754

  Danielmeier, Karsten ^a,b   Schierle, Kerstin ^b   Steckhan, Eberhard ^b  

^a BAYER AG   (Germany)

^b Inst fur Org Chem und B   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

2 OXAZOLIDINONE DERIVATIVE; AMINOALCOHOL; BENZENE DERIVATIVE; BORATE SODIUM; ELECTROLYTE; GRAPHITE; METHANOL; PROTEINASE INHIBITOR; SULFONIC ACID DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; DRUG SYNTHESIS; ELECTROCHEMISTRY; ELECTRODE; ENANTIOMER; OXIDATION; PH; PRECURSOR; PRIORITY JOURNAL;

EID: 0030586170     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00506-6     Document Type: Article

References (62)

1. 1. a) Shono, T. in: Comprehensive Org. Synt. (Vol 7), Trost, B. M.; Fleming, I. Eds., Pergamon Press, Oxford 1991, 789-815;
2. b) Shono, T. Tetrahedron 1984, 40, 811-850;
3. c) Shono, T. Electroorganic Synthesis, Academic Press, London 1990;
4. d) Shono, T. Top. Curr. Chem., Steckhan, E. Ed., 1988, 148, 131-151.
5. 2. Reißig, H. U. Nachr. Chem. Tech. Lab. 1986, 34, 656-659.
6. 3. a) Ross, S. D.; Finkelstein, M.; Petersen, R. C. J. Am. Chem. Soc. 1964, 86, 4139-4143;
7. b) Ross, S. D.; Finkelstein, M.; Petersen, R. C. J. Am. Chem. Soc. 1966, 88, 4657-4660;
8. c) Ross, S. D.; Finkelstein, M.; Petersen, R. C. J. Org. Chem. 1966, 31, 128-133;
9. d) Ruud, E. J.; Finkelstein, M.; Petersen, R. C. J. Org. Chem. 1972, 37, 1763-1767;
10. e) Nyberg, K. Synthesis 1976, 545-546.
11. 4. a) Brungs, P.; Danielmeier, K.; Jakobi, J.; Nothhelfer, C.; Stahl, A.; Zietlow, A.; Steckhan, E. J. de Chimie Physique 1996, in print;
12. b) Steckhan, E.; Brungs, P.; Zietlow, A.; Stahl, A.; Lewall, B.; Kardassis, G.; Papadopolos, A. in: Modem Methodology in Organic Synthesis, Shono, T. Ed.; Kodannsha, VCH, Tokyo, Weinheim 1992; p. 323-337;
13. c) Stahl, A. Ph.D thesis, Bonn, 1994;
14. d) Stahl, A.; Steckhan, E.; Nieger, M. Tetrahedron Lett. 1994, 35, 7371-7374.
15. 5. Shono, T.; Matsumura, Y.; Fujita, T. Tetrahedron Lett. 1991, 46, 6723-6726.
16. 6. a) Mori, M.; Kagechika, K.; Sasai, H.; Shibasaki, M. Tetrahedron 1991, 47, 531-532;
17. b) Mori, M.; Ban, Y.; Wakamatsu, T.; Okita, M. Heterocycles 1985, 23, 247-250.
18. 7. Thaning, M.; Wistrand, L. G. Helvetica Chim. Acta 1986, 69, 1711-1717.
19. 8. Rodrigues Pereira, E.; Spessel, V.; Prudhomme, M.; Martre, A.-M.; Mousset, G. Tetrahedron Lett. 1995, 14, 2479-2482.
20. 9. Travernier, D.; Van Damme, S.; Ricquier, P.; Anteunis, M. J. O. Bull. Chem. Soc. Belg. 1988, 97, 859-861.
21. 10. Matsumura, Y.; Tomita, T. Tetrahedron Lett. 1994, 35, 3737-3740.
22. 11. Manfré, F.; Pulicani, J. P. Tetrahedron: Asymmetry 1994, 5, 235-238.
23. 12. a) Cornille, F.; Slomczynska, U.; Smythe, M. L.; Beusen, D.; Moeller, K. D.; Marshall, G. R. J. Am. Chem. Soc. 1995, 117, 909-917;
24. b) Wong, L.; Moeller, K. D. J. Am. Chem. Soc. 1993, 115, 11434-11445;
25. c) Ruthledge, L. D.; Moeller, K. D. J. Org. Chem. 1992, 57, 6360;
26. d) Rothfus, S. L.; Moeller, K. D. Tetrahedron Lett. 1992, 33, 2913-2916.
27. 13. a) Shono, T.; Matsumura, Y.; Inoue, K. J. Org. Chem. 1983, 48, 1388-1389;
28. b) Ginzel, K.-D.; Brungs, P.; Steckhan, E. Tetrahedron 1989, 45, 1691-1701;
29. c) Papadopoulos, A.; Lewall, B.; Steckhan, E.; Ginzel, K.-D.; Knoch, F.; Nieger, M. Tetrahedron 1991, 47, 563-572.
30. 14. a) Schäfer, H. J. Top. Curr. Chem., Steckhan, E. Ed., 1990, 152, 91-151;
31. b) Herborn, C.; Zietlow, A.; Steckhan, E. Angew. Chem. 1989, 101, 1393-1394; Angew. Chem. Int. Ed. Engl. 1989, 28, 1399-1340.
32. b) Herborn, C.; Zietlow, A.; Steckhan, E. Angew. Chem. 1989, 101, 1393-1394; Angew. Chem. Int. Ed. Engl. 1989, 28, 1399-1340.
33. 15. Prücher, H. Gottschlich, R.; Haase, A., Stohrer, M., Seyfried, C.. Bioorg. Med. Chem. Lett, 1992, 2(2), 165-170.
34. 16. Jarreau, F. X.; Koenig, J. J.; Rovei, V. Eur. Pat. Appl. EP 511,031(CI. C07D263/24), 18. Oct. 1992, CAS 1993, 118, 147549z.
35. 17. Walsh, D. A.; Yanni, J. M. US. US 5,086,055 (CI. 514-252; A61K31/50), 04. Feb. 1992, CAS 1992, 116, 188072r.
36. 18. a) Gregory, W. A.; Brittelli, D. R.; Wang, C. L. J.; Wuonola, M. A.; McRipley, R. J.; Eustine, D. C.; Eberly, V. S.; Batholomev, D. T.; Slee, A. M.; Forbes, M. J. Med. Chem 1989, 32, 1673-1681;
37. b) Brittelli, D. R.; Eustine, D. C.; Batholomev, D. T.; Slee, A. M.; Feldmann, P. A.; Braun, L. J.; Borkowski, J. J. Drugs. Exp. Chim. Res. 1990, 16(4), 149.
38. 19. Danielmeier, K.; Steckhan, E. Tetrahedron: Asymmetry 1995, 6, 1181-1190.
39. MeOH because pH is commonly used only in aqueous solution. Pletcher and Fleischmann used the description "pH": Fleischmann, M.; Pletcher, D. in Reactions of Molecules at Electrodes, Hush, M. S. Ed.; Wiley Interscience, London 1971, p. 347-402.
40. MeOH to the anodic oxidation of saturated aliphatic esters was reported by Shono, T.; Matsumura, Y.; Onumura, O.; Yamada, Y. Synthesis 1987, 1099-1100.
41. 22. a) Boehm, H.-P.; Diehl, E.; Heck, W.; Sappok, R. Angew. Chem. 1964 76, 742-751; Angew. Chem. Int. Ed. Engl. 1964, 3, 669-678;
42. 22. a) Boehm, H.-P.; Diehl, E.; Heck, W.; Sappok, R. Angew. Chem. 1964 76, 742-751; Angew. Chem. Int. Ed. Engl. 1964, 3, 669-678;
43. b) Diaz A. F., in Organic Electrochemistry (Baizer, M. M.; Lund L. Eds.; Marcel Decker, Inc.): New York, 1991; p. 1363-1396,
44. c) McCreerym R. L.; Cline, K. K. in: Laboratory Techniques in Electroanalytical Chemistry, 2nd Ed., Kissinger, P. T.; Heineman, W. R. Eds., Marcel Dekker, Inc., New York 1996, p. 293-332.
45. 23. Watkins, B. F.; Behling, J. R.; Kariv, E.; Miller, L.L. J. Am. Chem. Soc. 1975, 97, 3549-3550.
46. 24. a) Beck, F. 8. Internationales Technisches Symposium; Anwendungstechnik Batterien unter besonderer Berücksichtigung der Notstromversorgung, München, March 1993;
47. b) Beck, F.; Boinowitz, T.; Krohn, H., Tormin, U. THer, E. Mol. Cryst. Liq. Cryst. Sci. Technol. Sect A 1994, 245, 77-182; CAS 1994, 121, 39109j.
48. b) Beck, F.; Boinowitz, T.; Krohn, H., Tormin, U. THer, E. Mol. Cryst. Liq. Cryst. Sci. Technol. Sect A 1994, 245, 77-182; CAS 1994, 121, 39109j.
49. 25. Wang, P.-C. Heterocycles 1985, 23, 2237-2238.
50. 26. Shono, T.; Matsumura, Y.; Tsubata, K. Org. Synth. 1985, 63, 206-213.
51. 27. a) Shono, T. Electroorganic Synthesis (Best Synthetic Methods), Academic Press, London 1991; p. 13;
52. b) Lee, J.; Feldberg, S. W.; White, H. Paper at the 45th Annual Meeting of the International Society of Electrochemistry, Porto, Portugal, 1994; Book of Abstracts Vol I: Abstr. K IV-9.
53. b) Lee, J.; Feldberg, S. W.; White, H. Paper at the 45th Annual Meeting of the International Society of Electrochemistry, Porto, Portugal, 1994; Book of Abstracts Vol I: Abstr. K IV-9.
54. 28. Matsumura, Y.;Tomita, T.; Sudoh, M.; Kise, N. Tetrahedron Lett. 1994, 35, 1271-1274.
55. 29. Danielmeier, K.; Schierle, K.; Steckhan, E. submitted for publication.
56. 30. a) D. E. Falvey, Robbins, R. J. Tetrahedron Lett. 1994, 35, 4943-4946;
57. b) Wolf, J. P.; Pfander, H. Helvetica Chim. Acta 1986, 69, 918-926;
58. c) Rich, D. H.; Sun, E. T.; Ulm. E. J. Med. Chem. 1980, 23, 27-33;
59. d) Poss, M. A.; Reid, J. A. Tetrahedron Lett., 1992, 33, 1411-1414;
60. e) Deng, J.; Hamada, Y.; Shioiri, T.; Matsunaga, S.; Fusetani, N. Angew. Chem. 1994, 106, 1811-1813; Angew. Chem. Int. Ed. Engl. 1994, 33, 1729-1731.
61. e) Deng, J.; Hamada, Y.; Shioiri, T.; Matsunaga, S.; Fusetani, N. Angew. Chem. 1994, 106, 1811-1813; Angew. Chem. Int. Ed. Engl. 1994, 33, 1729-1731.
62. 31. Kanjolia, R. K.; Gupta, V. D. Z. Naturforsch. 1980, 35B, 767-71.