Epoxide Formation by Indirect Electroreductive Coupling between Aldehydes or Ketones and Activated gem-Dichloro Compounds

S. Oudeyer; E. Léonel; J. P. Paugam; J.-Y. Nédélec

doi:10.1055/s-2004-815915

PAPER

Epoxide Formation by Indirect Electroreductive Coupling between Aldehydes or Ketones and Activated gem-Dichloro Compounds

S. Oudeyer, E. Léonel, J. P. Paugam*, J.-Y. Nédélec
LECSO-CNRS UMR 7582, Université Paris XII-Val de Marne, 2 à 8 rue H. Dunant, 94320 Thiais, France
Fax: +33(01)49781148; e-Mail: paugam@glvt-cnrs.fr;

Abstract

All articles of this category

Abstract

Epoxides are prepared by indirect electroreductive coupling of carbonyl compounds (aldehydes or ketones) and activated gem-dichloro compounds. This process is more efficient with aryl ketones than with aryl aldehydes. Though yields are only moderate, this method offers the valuable advantage of avoiding the use of strong bases or peroxides.

Key words

epoxides - coupling - aldehydes - ketones - condensation - reductions

Full Text

References

1 Sengmany S. Léonel E. Paugam JP. Nédélec J.-Y. Synthesis 2002, 533

2 Oudeyer S. Léonel E. Paugam JP. Nédélec J.-Y. Tetrahedron 2003, 59: 1073

3 Lynch BM. Pausacker KH. J. Chem. Soc. 1955, 1525

4 Gupta KC. Nigam RK. Srivastava N. Indian Curr. Sci. 1984, 53: 191

5a Heck RF. Org. React. 1982, 27: 345

5b Sho CS. Uemura S. J. Organomet. Chem. 1994, 465: 85

6 Bellucci G. Chiappe C. Cordoni A. Tetrahedron: Asymmetry 1996, 7: 197

7a Lane JF. Walters DR. J. Am. Chem. Soc. 1951, 73: 4234

7b Shaap AP. Siddiqui S. Prasad G. Palomino E. Sandison M. Tetrahedron 1985, 41: 2229

7c Simmamura O. Suzuki H. Bull. Chem. Soc. Jpn. 1954, 27: 231

8 Cope AC. Trumbull PA. Trumbull ER. J. Am. Chem. Soc. 1958, 80: 2844

9a Tiffeneau M. Levy J. Bull. Soc. Chim. Fr. 1931, 49: 1806

9b Kayser F. Ann. Chim. Paris 1936, 6: 144

9c Ogata Y. Tabushi I. J. Am. Chem. Soc. 1961, 83: 3440

9d Lazzeretti P. Taddei F. Torre G. Org. Magn. Resonance 1973, 5: 385

10 Frohn M. Wang ZX. Shi Y. J. Org. Chem. 1998, 63: 6425

11 Zadok E. Amar D. Mazur Y. J. Am. Chem. Soc. 1980, 102: 6370

12 Nishino H. Satoh H. Yamashita M. Kurosawa K. J. Chem. Soc., Perkin Trans. 2 1999, 1919

13 Comprehensive Organic Transformation, A Guide to Functional Group Preparation Larock RC. VCH; New York: 1989. p.457

14 Yamada T. Takai T. Rhode O. Mukaiyama T. Bull. Chem. Soc. Jpn. 1991, 64: 2109

15 Cainelli G. Tangari N. Umani Ronchi A. Tetrahedron 1972, 28: 3009

16 Kessar SV. Singh P. Kaur NP. Chawla U. Shulka K. Aggarwal P. Venugopal D. J. Org. Chem. 1991, 56: 3908

17 Delmond B. Pommier JC. Valade J. J. Organomet. Chem. 1972, 35: 91

18 Tamura Y. Bayomi SM. Sumoto K. Ikeda M. Synthesis 1977, 693

19 Johnson CR. Mori K. Nakanishi A. J. Org. Chem. 1979, 44: 2065

20a Corey EJ. Chaykovsky M. J. Am. Chem. Soc. 1962, 84: 867

20b Corey EJ. Oppolzer W. J. Am. Chem. Soc. 1964, 86: 1899

21 Hatch MJ. J. Org. Chem. 1969, 34: 2133

22a Aggarwal VK. Abdel-Rahman H. Fan L. Jones RVH. Standen MCH. Chem.-Eur. J. 1996, 8: 1024

22b Aggarwal VK. Alonso E. Hynd G. Lyndon KM. Palmer MJ. Porcelloni M. Studley JR. Angew. Chem. Int. Ed. 2001, 40: 1430

23 Padwa A. Gasdaska JR. Tetrahedron 1988, 44: 4147

24 Zhong K. Shao J. Liu C. Lu R. Synth. Commun. 1991, 21: 869

25 Shanklin JR. Johnson CR. Ollinger J. Coates RM. J. Am. Chem. Soc. 1973, 95: 3429

26 Durandetti M. Périchon J. Nédélec J.-Y. Tetrahedron Lett. 1999, 40: 9009

27 Léonel E. Paugam JP. Heintz M. Nédélec J.-Y. Synth. Commun. 1999, 29: 4015

28 Conan A. Sibille S. Périchon J. J. Org. Chem. 1991, 56: 2018

29 Fleisher R. Galle D. Braun M. Liebigs Ann. Recl. 1997, 1189

30 Inoue Y. Yamasaki N. Shimoyama H. Tai A. J. Org. Chem. 1993, 58: 1785

31 Murray RW. Singh M. Jeyaraman R. J. Am. Chem. Soc. 1992, 114: 1346

32 Bulman Page PC. Rassias GA. Bethell D. Schilling MB. J. Org. Chem. 1998, 63: 2774

33 Dansette PM. Ziffer H. Jerina DM. Tetrahedron 1976, 32: 2071

34 Zanardi J. Leriverend C. Aubert D. Julienne K. Metzer P. J. Org. Chem. 2001, 66: 5620

35 Fetizon M. Henry Y. Aranda G. Audier HE. De Luzes H. Org. Mass. Spectrom. 1974, 8: 201

36 Majima T. Tojo S. Ishida A. Takamuku S. J. Org. Chem. 1996, 61: 7793

37 Solladié-Cavallo A. Diep-Vohuule A. Sunjic V. Vinkovic V. Tetrahedron: Asymmetry 1996, 7: 1783

38 Solladié-Cavallo A. Lupattelli P. Marsol C. Isarno T. Bonini C. Caruso L. Maiorella A. Eur. J. Org. Chem. 2002, 1439