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-00000083.xml
Synlett 2007(17): 2683-2686
DOI: 10.1055/s-2007-991075
DOI: 10.1055/s-2007-991075
LETTER
© Georg Thieme Verlag Stuttgart · New YorkZr(DS)4 as an Efficient Catalyst for the Aminolysis of Epoxides in Water
Further Information
Received
29 May 2007
Publication Date:
25 September 2007 (online)
Publication History
Publication Date:
25 September 2007 (online)

Abstract
Zirconium dodecyl sulfate [Zr(DS)4] is an efficient catalyst for the aminolysis of epoxides in water at pH 5.0. Epoxides and anilines were used and the corresponding β-amino alcohols were isolated in generally high regioselectivity and excellent yields.
Key words
aqueous medium - aminolysis - epoxides - Zr(DS)4 - LASC - surfactants
- 1a
Bergmeier SC. Tetrahedron 2000, 56: 2561 - 1b
Ager DJ.Prakash I.Schaad DR. Chem. Rev. 1996, 96: 835 - 2a
Corey EJ.Zhang F. Angew. Chem. Int. Ed. 1999, 38: 1931 - 2b
Johannes CW.Visser MS.Weatherhead GS.Hoveyda AM. J. Am. Chem. Soc. 1998, 120: 8340 - 2c
Chng BL.Ganesan A. Bioorg. Med. Chem. Lett. 1997, 7: 1511 - 2d
Coppola GM.Schuster HF. Asymmetric Synthesis. Construction of Chiral Molecules Using Amino Acids Wiley; New York: 1987. - 3a
O’Brien P. Angew. Chem. Int. Ed. 1999, 38: 326 - 3b
Li G.Chang H.-T.Sharpless KB. Angew. Chem., Int. Ed. Engl. 1996, 35: 451 - 4
Noyori R. Asymmetric Catalysis in Organic Synthesis John Wiley and Sons; New York: 1994. - Literature examples in this field are countless; for some recent examples, see:
- 5a
Yarapathy VR.Mekala S.Rao BV.Tammishetti S. Catal. Commun. 2006, 7: 466 - 5b
Williams DGB.Lawton M. Tetrahedron Lett. 2006, 47: 6557 - 5c
Kamal A.Ramu R.Amerudin Azhar M.Ramesh Khanna GB. Tetrahedron Lett. 2005, 46: 2675 - 5d
Placzek AT.Donelson JL.Trivedi R.Gibbs RA.De SK. Tetrahedron Lett. 2005, 46: 9029 - 5e
Zhao P.-Q.Xu L.-W.Xia C.-G. Synlett 2004, 846 - 5f
Carree F.Gil R.Collin J. Tetrahedron Lett. 2004, 45: 7749 - 5g
Rodriquez JR.Navarro A. Tetrahedron Lett. 2004, 45: 7495 - 5h
Sundrarajan G.Vijayakrishna K.Varghese B. Tetrahedron Lett. 2004, 45: 8253 - 5i
Ollevier T.Lavie-Compin G. Tetrahedron Lett. 2004, 45: 49 - 5j
Chakraborti AK.Rudrawar S.Kondaskar A. Org. Biomol. Chem. 2004, 2: 1277 - 5k
Chakraborti AK.Kondaskar A. Tetrahedron Lett. 2003, 44: 8315 - 6a
Organic Synthesis in Water
Lindström UM. Blackwell; Oxford: 2007. - 6b
Li C.-J. Chem. Rev. 2005, 105: 3095 - 6c
Lindström UM. Chem. Rev. 2002, 102: 2751 - 6d
Manabe K.Kobayashi S. Chem. Eur. J. 2002, 8: 4095 - 6e
Fringuelli F.Piermatti O.Pizzo F.Vaccaro L. Eur. J. Org. Chem. 2001, 439 - 6f
Organic Synthesis in Water
Grieco PA. Blackie Academic and Professional; London: 1998. - 6g
Li CJ.Chang TH. In Organic Reactions in Aqueous Media Wiley; New York: 1997. - 7
Kolb HC.Finn MG.Sharpless KB. Angew. Chem. Int. Ed. 2001, 40: 2004 - 8a
Fringuelli F.Pizzo F.Tortoioli S.Vaccaro L. Org. Lett. 2005, 7: 4411 - 8b
Fringuelli F.Pizzo F.Vaccaro L. J. Org. Chem. 2004, 69: 2315 - 8c
Fringuelli F.Pizzo F.Tortoioli S.Vaccaro L. Green Chem. 2003, 5: 436 - 8d
Fringuelli F.Pizzo F.Tortoioli S.Vaccaro L. J. Org. Chem. 2003, 68: 8248 - 8e
Fringuelli F.Pizzo F.Rucci M.Vaccaro L. J. Org. Chem. 2003, 68: 7041 - 8f
Fringuelli F.Pizzo F.Tortoioli S.Vaccaro L. Adv. Synth. Catal. 2002, 344: 379 - 8g
Fringuelli F.Pizzo F.Vaccaro L. J. Org. Chem. 2001, 66: 3554 - 8h
Fringuelli F.Pizzo F.Vaccaro L. J. Org. Chem. 2001, 66: 4719 - 8i
Fringuelli F.Piermatti O.Pizzo F.Vaccaro L. J. Org. Chem. 1999, 64: 6094 - 9a
Bonollo S.Fringuelli F.Pizzo F.Vaccaro L. Green Chem. 2006, 8: 960 - 9b
Wu J.Xia H.-G. Green Chem. 2005, 7: 708 - 9c
Surendra K.Krishnaveni NS.Rao KR. Synlett 2005, 506 - 9d
Azizi M.Saidi MR. Org. Lett. 2005, 7: 3649 - 10
Azoulay S.Manabe K.Kobayashi S. Org. Lett. 2005, 7: 4593 - As representative examples, see:
- 11a
Boudou M.Ogawa C.Kobayashi S. Adv. Synth. Catal. 2006, 348: 2585 - 11b
Kobayashi S.Manabe K. Acc. Chem. Res. 2002, 35: 209 - 11c
Manabe K.Mori Y.Wakabayashi T.Nagayama W.Kobayashi S. J. Am. Chem. Soc. 2000, 122: 7202 - 11d
Kobayashi S.Mori Y.Nagayama W.Manabe K. Green Chem. 1999, 1: 175 - 12
Otto S.Engberts JBFN.Kwak JCT. J. Am. Chem. Soc. 1998, 120: 9517 - 13a
Fioroni G.Fringuelli F.Pizzo F.Vaccaro L. Green Chem. 2003, 5: 425 - 13b
Fringuelli F.Pizzo F.Tortoioli S.Vaccaro L. J. Org. Chem. 2003, 68: 8248 - 13c
Amantini D.Fringuelli F.Pizzo F.Tortoioli S.Vaccaro L. Synlett 2003, 2292 - 13d
Fringuelli F.Pizzo F.Vaccaro L. Tetrahedron Lett. 2001, 41: 1131 - 13e
Amantini D.Fringuelli F.Pizzo F.Vaccaro L. Green Chem. 2001, 3: 229 - 13f
Amantini D.Fringuelli F.Pizzo F.Vaccaro L. J. Org. Chem. 2001, 66: 4463 - 13g
Fringuelli F.Pizzo F.Vaccaro L. Synlett 2000, 311
References and Notes
The pH value reported is that measured in the clear aqueous layer completely separated from the organic one. A pH meter equipped with a combined refillable pH electrode and with an autocompensating temperature control (ATC) probe was used.