Electrochemical oxidation of (R)-4-hydroxy-2-pyrrolidone: A key building block for stereoselective N-acyliminium ion coupling reactions

Tetrahedron

Volumn 55, Issue 50, 1999, Pages 14407-14420

  Lennartz, Michael ^a   Sadakane, Masahiro ^a   Steckhan, Eberhard ^a  

^a UNIVERSITY OF BONN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRROLIDONE DERIVATIVE; METHANOL;

ALKYLATION; ARTICLE; DIASTEREOISOMER; ELECTROCHEMICAL ANALYSIS; OXIDATION; PRIORITY JOURNAL;

EID: 0033544812     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00904-7     Document Type: Article

References (22)

1. a) Shono, T. Tetrahedron 1984, 40, 811;
2. b) Shono, T. Top. Curr. Chem., Steckhan, E. Ed., 1988, 148, 131;
3. c) Steckhan, E.; Brungs, P.; Zietlow, A.; Stahl, A.; Lewall, B.; Kardassis, G.; Papadopolos, A. in Modern Methodology in Organic Synthesis, Shono, T. Ed.; Kodannsha, VCH, Tokyo, Weinheim 1992; p. 323;
4. d) Danielmeier, K.; Kolter, D.; Sadakane, M.; Schierle, K.; Stahl, A.; Vahle, R.; Zietlow, A.; Steckhan, E. in Novel Trends in Electroorganic Synthesis, Torii, S. Ed., Springer, Tokyo 1998; p. 55;
5. e) Steckhan, E.; Danielmeier, K.; Kolter, D.; Lennartz, M.; Sadakane, M.; Schierle, K.; Vahle, R.; Zietlow, A. GDCh-monographie, Vol. 14, Frankfurt am Main 1999, p. 164.
6. a) Shono, T.; Matsumura, Y.; Inoue, K. J. Org. Chem. 1983, 48, 1388;
7. b) Ginzel, K.D.; Brungs, P.; Steckhan, E. Tetrahedron 1989, 45, 1691.
8. a) Schäfer, H.J. Top. Curr. Chem., Steckhan, E. Ed., 1990, 152, 91;
9. b) Zietlow, A., Steckhan, E. J. Org. Chem. 1994, 59, 5658.
10. a) Michael, J.P. Nat. Prod. Rep. 1996, 13, 21;
11. b) Michael, J.P. Nat. Prod. Rep. 1995, 12, 535;
12. c) Wong, C.-H.; Halcomb, R.L.; Ichibaka, Y.; Kajimoto, T. Angew. Chem. Int. Ed. Engl. 1995, 34, 521.
13. The electrochemical oxidation of the O-TBDMS derivative of 1 resulted in poor yields maybe because of sterical reasons.
14. Danielmeier, K.; Schierle, K.; Steckhan, E. Tetrahedron 1996, 52, 9743.
15. Shono, T. Electroorganic Synthesis (Best Synthetic Methods), Academic Press, London 1991; p. 13.
16. Hiemstra, H.; Speckamp, W.N. in Comprehensive Organic Synthesis, Trost, B.M.; Fleming, I. Eds., Vol. 2, Pergamon Press, Oxford 1991, p. 1047.
17. de Koning, H.; Hiemstra, H.; Moolenaar, M.J.; Speckamp, W.N. Eur. J. Org. Chem. 1998, 1729.
18. Thaning, M.; Wistrand, L.-G. Acta Chem. Scand. 1989, 43, 290.
19. Renaud, P.; Seebach, D. Helv. Chim. Acta 1986, 69, 1704.
20. Ryu, Y.; Kim, G. J. Org. Chem. 1995, 60, 103.
21. Dale, J.A.; Mosher, H.S. J. Am. Chem. Soc. 1973, 95, 512.
22. The atomic co-ordinates for this work are available on request from the Director of the Cambridge Crystallographic Data Centre, University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW. Any request should be accompanied by the full literature citation for this communication.