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Synthesis 2003(18): 2753-2762
DOI: 10.1055/s-2003-44359
DOI: 10.1055/s-2003-44359
REVIEW
© Georg Thieme Verlag Stuttgart · New York
Epoxide Oxidations: A Valuable Tool in Organic Synthesis
Further Information
Received
18 June 2003
Publication Date:
10 December 2003 (online)
Publication History
Publication Date:
10 December 2003 (online)
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
- 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, andFuruhashi 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 - 61
Sword IP. J. Chem. Soc. (C) 1971, 820 - 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, andAntoniotti 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