Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2005(19): 3405-3411
DOI: 10.1055/s-2005-918483
DOI: 10.1055/s-2005-918483
PAPER
© Georg Thieme Verlag Stuttgart · New YorkHighly Efficient Catalysts for Epoxidation Mediated by Iminium Salts
Further Information
Received
9 September 2005
Publication Date:
14 November 2005 (online)
Publication History
Publication Date:
14 November 2005 (online)
Abstract
A range of substituted dihydroisoquinolinium salts has been tested in the catalytic epoxidation of several alkenes. Catalyst loadings as low as 0.5 mol% have been used in the epoxidation of 1-phenylcyclohexene.
Key words
catalysis - epoxidations - oxidations - iminium salt - oxaziridinium salt
- 1a
Sharpless KB. Aldrichimica Acta 1983, 16: 67 - 1b
Gorzynski Smith J. Synthesis 1984, 629 - 1c
Behrens CH.Katsuki T. Coord. Chem. Rev. 1995, 140: 189 - See, for example:
- 2a
Paquette LA.Gao Z.Ni Z.Smith GF. J. Am. Chem. Soc. 1998, 120: 2543 - 2b
Amano S.Ogawa N.Ohtsuka M.Chida N. Tetrahedron 1999, 55: 2205 - 3
Dalko PI.Moisan L. Angew. Chem. Int. Ed. 2004, 43: 5138 - 4a
Yang D.Yip Y.-C.Tang M.-W.Wong M.-K.Zheng J.-H.Cheung K.-K. J. Am. Chem. Soc. 1996, 118: 491 - 4b
Yang D.Wang XC.Wong M.-K.Yip Y.-C.Tang M.-W. J. Am. Chem. Soc. 1996, 118: 11311 - 4c
Yang D.Wong M.-K.Yip Y.-C.Wang XC.Tang M.-W.Zheng J.-H.Cheung K.-K. J. Am. Chem. Soc. 1998, 120: 5943 - 4d
Yang D.Yip Y.-C.Chen J.Cheung K.-K. J. Am. Chem. Soc. 1998, 120: 7659 - 4e
Yang D.Yip Y.-C.Jiao G.-S.Wong M.-K. J. Org. Chem. 1998, 63: 8952 - 4f
Yang D.Yip Y.-C.Tang M.-W.Wong M.-K.Cheung K.-K. J. Org. Chem. 1998, 63: 9888 - 4g
Yang D.Jiao G.-S.Yip Y.-C.Wong M.-K. J. Org. Chem. 1999, 64: 1635 - 4h
Yang D.Tang Y.-C.Chen J.Wang X.-C.Bartberger MD.Houk KN.Olson L. J. Am. Chem. Soc. 1999, 121: 11976 - 4i
Yang D. Acc. Chem. Res. 2004, 37: 497 - 4j
Armstrong A.Hayter BR. Chem. Commun. 1998, 621 - 4k
Armstrong A.Hayter BR. Tetrahedron 1999, 55: 11119 - 4l
Armstrong A.Hayter BR.Moss WO.Reeves JR.Wailes JS. Tetrahedron: Asymmetry 2000, 11: 2057 - 4m
Armstrong A.Moss WO.Reeves JR. Tetrahedron: Asymmetry 2001, 12: 2779 - 4n
Armstrong A.Ahmed G.Dominguez-Fernandez B.Hayter BR.Wailes SJ. J. Org. Chem. 2002, 67: 8610 - 5a
Davis FA.Abdul-Malik NF.Awad SB.Haracal ME. Tetrahedron Lett. 1981, 22: 917 - 5b
Davis FA.Towson JC.Weismiller MC.Lal S.Caroll PJ. J. Am. Chem. Soc. 1988, 110: 8477 - 5c
Davis FA.Haracal ME.Awad SB. J. Am. Chem. Soc. 1983, 105: 3123 - 5d
Davis FA.Przeslawski RM. Abstracts of Papers, 201st National Meeting of the American Chemical Society, Atlanta American Chemical Society; Washington, DC: 1991. p.ORGN0105 - 5e
Davis FA.Haque MS. J. Org. Chem. 1986, 51: 4083 - 5f
Davis FA.Vishwakarma LC.Billmers JM. J. Org. Chem. 1984, 49: 3241 - 5g
Davis FA.Sheppard AC. J. Org. Chem. 1987, 52: 954 - 5h
Davis FA.Lal SG.Durst HD. J. Org. Chem. 1988, 53: 5004 - 5i
Davis FA.Towson JC.Weismiller MC.Lal SG.Caroll PJ. J. Am. Chem. Soc. 1988, 110: 8477 - 5j
Page PCB.Graham AE.Bethell D.Park BK. Synth. Commun. 1993, 23: 1507 - 5k
Page PCB.Bethell D.Heer JP.Collington EW.Andrews DM. Tetrahedron Lett. 1994, 35: 9629 - 5l
Page PCB.Heer JP.Bethell D.Collington EW.Andrews D. Synlett 1995, 773 - 5m
Andrews DM.Bethell D.Collington EW.Heer JP.Page PCB. Tetrahedron: Asymmetry 1995, 6: 2911 - 5n
Page PCB.Heer JP.Bethell D.Lund A.Collington EW.Andrews DM. J. Org. Chem. 1997, 62: 6093 - 5o
Page PCB.Bethell D.Stocks PA.Heer JP.Graham AE.Vahedi H.Healy M.Collington EW.Andrews DM. Synlett 1997, 1355 - 5p
Page PCB.Bethell D.Vahedi H. J. Org. Chem. 2000, 65: 6756 - 6a
Picot A.Millet P.Lusinchi X. Tetrahedron Lett. 1976, 17: 1573 - 6b
Hanquet G.Lusinchi X.Milliet P. Tetrahedron Lett. 1987, 28: 6061 - 6c
Hanquet G.Lusinchi X.Milliet P. Tetrahedron Lett. 1988, 29: 3941 - 7a
Bohé L.Hanquet G.Lusinchi M.Lusinchi X. Tetrahedron Lett. 1993, 34: 7271 - 7b
Bohé L.Lusinchi M.Lusinchi X. Tetrahedron 1999, 55: 141 - 7c
Gluszynska A.Mackowska I.Rozwadowska MD.Sienniak W. Tetrahedron: Asymmetry 2004, 15: 2499 - 7d
Aggarwal VK.Wang MF. J. Chem. Soc., Chem. Commun. 1996, 191 - 7e
Armstrong A.Ahmed G.Garnett I.Gioacolou K. Synlett 1997, 1075 - 7f
Armstrong A.Ahmed G.Garnett I.Gioacolou K.Wailes JS. Tetrahedron 1999, 55: 2341 - 7g
Minakata S.Takemiya A.Nakamura K.Ryu I.Komatsu M. Synlett 2000, 1810 - 7h
Wong M.-K.Ho L.-M.Zheng Y.-S.Ho C.-Y.Yang D. Org. Lett. 2001, 16: 2587 - 7i
Lacour J.Monchaud D.Marsol C. Tetrahedron Lett. 2002, 43: 8257 - 7j
Vachon J.Pérollier C.Monchaud D.Marsol C.Ditrich K.Lacour J. J. Org. Chem. 2005, 70: 5903 - 8a
Bohé L.Kammoun M. Tetrahedron Lett. 2002, 43: 803 - 8b
Bohé L.Kammoun M. Tetrahedron Lett. 2004, 45: 747 - 9a
Page PCB.Rassias GA.Bethell D.Schilling MB. J. Chem. Soc., Perkin Trans. 1 2000, 3325 - 9b
Page PCB.Rassias GA.Barros D.Ardakani A.Buckley B.Bethell D.Smith TAD.Slawin AMZ. J. Org. Chem. 2001, 66: 6926 - 9c
Page PCB.Rassias GA.Barros D.Ardakani A.Bethell D.Merrifield E. Synlett 2002, 580 - 9d
Page PCB.Barros D.Buckley BR.Ardakani A.Marples BA. J. Org. Chem. 2004, 69: 3595 - 9e
Page PCB.Buckley BR.Heaney H.Blacker AJ. Org. Lett. 2005, 7: 375 - 9f
Page, P. C. B.; Buckley, B. R.; Rassias, G. A.; Blacker, A. J. Eur. J. Org. Chem. 2005, in press.
- 10
Page PCB.Buckley BR.Blacker AJ. Org. Lett. 2004, 6: 1543 - 11a
Taj SS.Soman R. Tetrahedron: Asymmetry 1994, 5: 1513 - 11b
Hassine B.Gorsane M.Greets-Evrard F.Pecher J.Martin RH.Castelet D. Bull. Soc. Chim. Belg. 1986, 95: 547 - 12a
Sasaki H.Irie R.Hamada T.Suzuki K.Katsuki T. Tetrahedron 1994, 50: 11827 - 12b
Boyd DR.Sharma ND.Bowers NI.Goodrich PA.Groocok RM. Tetrahedron: Asymmetry 1996, 7: 1559 - 12c
Sola L.Vidal-Ferran A.Moyano A.Pericas MA.Riera A. Tetrahedron: Asymmetry 1997, 8: 1559 - 13a
Fleiser R.Galle D.Braun M. Liebigs Ann. 1997, 6: 1189 - 13b
Tu Y.Wang Z.-X.Shi Y. J. Am. Chem. Soc. 1996, 118: 9806 - 13c
Brandes BD.Jacobsen EN. J. Org. Chem. 1994, 59: 4378 - 13d
Belluci G. J. Chem. Soc., Perkin Trans. 2 1973, 292 - 14
Melloni P.Della Torre A.Lazzari E.Mazzini G.Meroni M. Tetrahedron 1985, 41: 1393 - 15
Tian H.She X.Yu H.Shu L.Shi Y. J. Org. Chem. 2002, 67: 2435 - 16a
Kurth MJ.Abreo MA. Tetrahedron 1990, 46: 5085 - 16b
Krief A.Heresi L.Nagy JB.Derouane EG. Angew. Chem. 1977, 89: 103 - 16c
Chiappe C.Cordoni A.Lo Moro G.Palese CD. Tetrahedron: Asymmetry 1998, 9: 341