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Synthesis 2009(16): 2790-2796
DOI: 10.1055/s-0029-1216899
DOI: 10.1055/s-0029-1216899
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Aminolysis of Epoxides Using Iridium Trichloride as an Efficient Catalyst
Weitere Informationen
Received
6 April 2009
Publikationsdatum:
14. Juli 2009 (online)
Publikationsverlauf
Publikationsdatum:
14. Juli 2009 (online)
Abstract
Iridium trichloride catalyzes the ring opening of epoxides by aryl, heterocyclic, or aliphatic amines under mild conditions. The reactions proceed at room temperature to afford the corresponding β-amino alcohols in excellent yields. In general, the aminolysis of cyclopentene oxide is faster than that of cyclohexene oxide in the presence of iridium trichloride as a catalyst.
Key words
epoxides - iridium trichloride - amines - amino alcohols - aminolysis
- Supporting Information for this article is available online:
- Supporting Information
-
1a
Kunieda T.Ishizuka T. In Studies in Natural Product Chemistry Vol. 12:Rahman A. Elsevier; Amsterdam: 1993. p.411-445 -
1b
Ager DJ.Prakash I.Schaad DR. Chem. Rev. 1996, 96: 835 -
1c
Bergmeier SC. Tetrahedron 2000, 56: 2561 -
2a
Rogers GA.Parsons SM.Anderson DC.Nilsson LM.Bahr BA.Kornreich WD.Kaufman R.Jacobs RS.Kirtman B. J. Med. Chem. 1989, 32: 1217 -
2b
Chng BL.Ganesan A. Bioorg. Med. Chem. Lett. 1997, 7: 1511 -
3a
Sekar G.Singh VK. J. Org. Chem. 1999, 64: 287 -
3b
Ollevier T.Lavie-Compin G. Tetrahedron Lett. 2004, 45: 49 -
3c
Khosropour AR.Khodaei MM.Ghozati K. Chem. Lett. 2004, 33: 304 -
3d
Williams DBG.Lawton M. Tetrahedron Lett. 2006, 47: 6557 -
4a
Chandrasekhar S.Ramachandar T.Prakash JS. Synthesis 2000, 1817 -
4b
Reddy LR.Reddy MA.Bhanumathi N.Rao KR. New J. Chem. 2001, 25: 221 -
4c
Ollevier T.Lavie-Compin G. Tetrahedron Lett. 2002, 43: 7891 -
4d
Sabitha G.Reddy GSKK.Reddy KB.Yadav JS. Synthesis 2003, 2298 -
4e
Chakraborti AK.Kondaskar A. Tetrahedron Lett. 2003, 44: 8315 -
4f
Rodríguez JR.Navarro A. Tetrahedron Lett. 2004, 45: 7495 -
4g
Sundararajan A.Vijayakrishna K.Varghese B. Tetrahedron Lett. 2004, 45: 8253 - 5
Kamal A.Ramu RR.Azhar MA.Khanna GBR. Tetrahedron Lett. 2005, 46: 2675 - 6
.
Pujala B.Chakraborti AK. J. Org. Chem. 2007, 72: 3713 - 7
Azizi N.Saidi MR. Tetrahedron 2007, 63: 888 - 8
Yadav JS.Reddy BVS.Basak AK.Narasaiah AV. Tetrahedron Lett. 2003, 44: 1047 - 9
Das U.Crousse B.Kesavan V.Bonnet-Delpon D.Bégué J.-P. J. Org. Chem. 2000, 65: 6749 - 10
Curini M.Epifano F.Marcotullio MC.Rosati O. Eur. J. Org. Chem. 2001, 4149 - 11
Mojtahedi MM.Abaee MS.Hamidi V. Catal. Commun. 2007, 8: 1671 - 12
Singh MC.Peddinti RK. Tetrahedron Lett. 2007, 48: 7354 - 13
Ghazanfari D.Hashemi MM.Mottaghi MM.Foroughi MM. J. Chem. Res. 2008, 220 - 14
Takeuchi R.Kezuka S. Synthesis 2006, 3349 - 15
Helmchen G.Dahnz A.Dübon P.Schelwies M.Weihofen R. Chem. Commun. 2007, 675 - 16
Roseblade SJ.Pfaltz A. Acc. Chem. Res. 2007, 40: 1402 - 17
Cui X.Burgess K. Chem. Rev. 2005, 105: 3272 - 18
Karamé I.Tommasino ML.Lemaire M. Tetrahedron Lett. 2003, 44: 7687