Epoxide Oxidations: A Valuable Tool in Organic Synthesis

Sylvain Antoniotti; Elisabet Duñach

doi:10.1055/s-2003-44359

REVIEW

Epoxide Oxidations: A Valuable Tool in Organic Synthesis

Sylvain Antoniotti^a, Elisabet Duñach*^a,b
^a Faculté des Sciences, Laboratoire Arômes, Synthèses et Interactions, Université de Nice-Sophia Antipolis,, Parc Valrose 06108, Nice cedex 2, France
^b Faculté des Sciences, Laboratoire de Chimie Bio-Organique, UMR CNRS 6001, Université de Nice-Sophia Antipolis, Parc Valrose 06108, Nice cedex 2, France
Fax: +33(4)92076151.; e-Mail: dunach@unice.fr.;

Abstract

All articles of this category

Abstract

This article focuses on stoichiometric and catalytic epoxide oxidations and their scope in organic synthesis. The work on Bi/O₂-catalysed oxidation, developed in our group over the last last ten years, is presented with various reactions leading to several oxidised compounds.

1 Introduction

2 Epoxide Oxidations Involving C-C Bond Cleavage

2.1 Stoichiometric Oxidations

2.2 Catalytic Oxidations

3 Epoxide Oxidations Without C-C Bond Cleavage

3.1 Stoichiometric Oxidations

3.2 Catalytic Oxidations

4 Conclusion

Key words

epoxides - oxidations - catalysis - bismuth - oxygen

Full Text

References

1 Lane BS. Burgess K. Chem. Rev. 2003, 103: 2457

2 See for example: Aggarwal VK. Harvey JN. Richardson J. J. Am. Chem. Soc. 2002, 124: 5747

3 March J. Advanced Organic Chemistry Wiley-Interscience; New-York: 1992. 4th Ed.. p.1174

4 Hodgson DM. Gras E. Synthesis 2002, 1625

5 Katsuki T. Sharpless BK. J. Am. Chem. Soc. 1980, 102: 5974

6 Zhang W. Loebach JL. Wilson SR. Jacobsen EN. J. Am. Chem. Soc. 1990, 112: 2801

7 For a review on enantioselective oxidation of olefins see: Bonini C. Righi G. Tetrahedron 2002, 58: 4981

8 Jacobsen EN. Wu MH. Comprehensive Asymmetric Catalysis I-III Springer-Verlag; Berlin: 1999. p.1309

9 Fatiadi AJ. Synthesis 1974, 229

10 Maerker G. Haeberer ET. J. Am. Oil Chem. Soc. 1966, 43: 97

11 Nagarkatti JP. Ashley KR. Tetrahedron Lett. 1973, 46: 4599

12 Sharma A. Chattopadhyay S. Liebigs Ann. 1996, 4: 529

13 Trivedi SV. Mamdapur VR. Indian J. Chem., Sect. B 1986, 25: 176

14 Kurosawa M. Kanamaru H. Nishioka K. J. Labelled Compd. Radiopharm. 1997, XXXIX: 129

15 Goldbach M. Jäkel E. Schneider MP. J. Chem. Soc., Chem. Commun. 1987, 1434

16 Johnson AE. Nursten HE. Williams AA. Chem. Ind. 1971, 556: 1212

17 Bartlett PD. Banavali R. J. Org. Chem. 1991, 56: 6043

18 Paquette LA. Künzer H. Green KE. De Lucchi O. Licini G. Pasquato L. Valle G. J. Am. Chem. Soc. 1986, 108: 3453

19 Paquette LA. Fischer JW. Browne AR. Doecke CW. J. Am. Chem. Soc. 1985, 107: 686

20 Attygalle AB. Morgan ED. Anal. Chem. 1983, 55: 1379

21 Attygalle AB. Morgan ED. Anal. Chem. 1984, 56: 1530

22a Ferreira JTB. Brocksom TJ. Braga AL. Quim. Nova 1982, 5: 4

22b Brocksom TJ. Ferreira JTB. Braga AL. J. Chem., Res. Synop. 1981, 10: 334

23 Roy SC. Adhikari S. Indian J. Chem., Sect. B 1992, 31: 459

24 Mandal AK. Borude DP. Synth. Commun. 1991, 21: 111

25 Curci R. Lopez L. Troisi L. Rashid KSM. Schaap PA. Tetrahedron Lett. 1988, 29: 3145

26 Bonchio M. Conte V. Di Furia F. Modena G. J. Mol. Catal. 1991, 71: 159

27 Ogata Y. Sawaki Y. Shimizu H. J. Org. Chem. 1978, 43: 1760

28 Hoffman J. J. Am. Chem. Soc. 1957, 79: 503

29 Temple RD. J. Org. Chem. 1970, 35: 1275

30 Mayeda EA. Miller LL. Wolf JF. J. Am. Chem. Soc. 1972, 94: 6812

31 Shono T. Matsumura Y. Hashimoto T. Hibino K. Hamaguchi H. Aoki T. J. Chem. Soc. 1975, 97: 2546

32 Torii S. Uneyama K. Tanaka H. Tsunao Y. Ono M. Kohmoto Y. J. Org. Chem. 1981, 46: 3312

33 Torii S. Inokuchi T. Oi R. J. Org. Chem. 1983, 48: 1944

34 Zevaco T. Duñach E. Postel M. Tetrahedron Lett. 1993, 34: 2601

35 Zevaco T. Postel M. Synth. React. Inorg. Met.-Org. Chem. 1992, 22: 289

36 Coin C. Zevaco T. Duñach E. Postel M. Bull. Soc. Chim. Fr. 1996, 133: 913

37 Le Boisselier V. Duñach E. Postel M. J. Organomet. Chem. 1994, 482: 119

38 Kallal K. Coin C. Duñach E. Postel M. New J. Chem. 1997, 21: 495

39 Coin C. Le Boisselier V. Favier I. Postel M. Duñach E. Eur. J. Org. Chem. 2001, 735

40 Favier I. G iulieri F. Duñach E. Hebrault D. Desmurs J.-R. Eur. J. Org. Chem. 2002, 1984

41 Barusch MR. Payne JQ. J. Am. Chem. Soc. 1953, 75: 1987

42 Kropf H. Ball M. Schröder H. Witte G. Tetrahedron 1974, 30: 2943

43 Ismail N. Rao RN. Chem. Lett. 2000, 844

44 Mancuso AJ. Swern D. Synthesis 1981, 165

45 Omura K. Swern D. Tetrahedron 1978, 34: 1651

46 Raina S. Bhuniya D. Singh VK. Tetrahedron Lett. 1992, 33: 6021

47 Raina S. Singh VK. Tetrahedron 1995, 51: 2467

48 Olah GA. Vankar YD. Arvanaghi M. Tetrahedron Lett. 1979, 38: 3653

49 Vankar YD. Saksena RK. Bawa A. Chem. Lett. 1989, 7: 1241

50 Vankar YD. Shah K. Bawa A. Singh SP. Tetrahedron 1991, 47: 8883

51 Gala D. DiBenedetto DJ. Tetrahedron Lett. 1994, 35: 8299

52 Vankar YD. Singh SP. Chem. Lett. 1986, 11: 1939

53a Katagiri T. Obara F. Toda S. Furuhashi K. Synlett 1994, 507

53b Katagiri T, and Furuhashi K. inventors; Nitsuko Kyoseki Kk Japan JP 05078278.

54 Cohen T. Tsuji T. J. Org. Chem. 1961, 26: 1681

55 Tsuji T. Bull. Chem. Soc. Jpn. 1989, 62: 645

56 Santosusso TM. Swern D. J. Org. Chem. 1975, 40: 2764

57 Trost BM. Fray JM. Tetrahedron Lett. 1988, 29: 2163

58 Villemin D. Hammadi M. Synth. Commun. 1995, 25: 3141

59 Marmer WN. Swern D. Tetrahedron Lett. 1969, 7: 531

60 Marmer WN. Swern D. J. Am. Chem. Soc. 1971, 93: 2719

62 Le Boisselier V. Postel M. Duñach E. Chem. Commun. 1997, 95

63 Tascedda P. Duñach E. J. Chem. Soc., Chem. Commun. 1995, 43

64 Tascedda P. Duñach E. Heterocycl. Commun. 1997, 3: 427

65 Tascedda P. Duñach E. Synlett 2000, 245

66 Antoniotti S. Duñach E. Chem. Commun. 2001, 2566

67 Antoniotti S. Duñach E. J. Mol. Catal. A. in press

68 Duñach E, and Antoniotti S. inventors; Rhodia Chimie, PCT/WO 03/022789 A2.

69 Antoniotti S. Duñach E. Tetrahedron Lett. 2002, 43: 3971

70 Gazit A. App H. McMahon G. Chen J. Levitzki A. Bohmer FD. J. Med. Chem. 1996, 39: 2170