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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Letter Article

Cu-Fe Spinels: First Heterogeneous and Magnetically Recoverable Catalyst for the Ferrier Rearrangement of 2-Nitroglycals

Author(s): Leticia Lafuente, María Florencia Rochetti, Rodolfo Bravo, Leandro Sasiambarrena, Cintia C. Santiago and Agustín Ponzinibbio*

Volume 16, Issue 6, 2019

Page: [447 - 453] Pages: 7

DOI: 10.2174/1570178615666181022145338

Price: $65

Abstract

Cu-Fe spinels promoted the Ferrier rearrangement of 2-nitroglycals with several O-nucleophiles. 2,3-Unsaturated carbohydrate derivatives were prepared by the reaction of 3,4,6-tri-Oacetyl- 2-nitroglucal and alcohols in the presence of 5 % of CuFe2O4. After separation of the catalyst with an external magnet, the reaction products were obtained in good yields and high stereo and regioselectivity. Also, S- and heterocyclic C-3 substituted 2-nitro-endo-glycals could be prepared by this method.

Keywords: 2-Nitroglycals, Cu-Fe spinels, Ferrier rearrangement, magnetically recoverable catalyst, unsaturated heterocycle, carbohydrate.

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[1]
Delaunay, T.; Poisson, T.; Jubault, P.; Pannecoucke, X. Eur. J. Org. Chem., 2014, 34, 7525-7546.
[2]
Pachamuthu, K.; Schmidt, R.R. Synlett, 2003, 9, 1355-1357.
[3]
Khodair, A.I.; Pachamuthu, K.; Schmidt, R.R. Synthesis, 2004, 1, 53-58.
[4]
Khodair, A.I.; Schmidt, R.R. Eur. J. Org. Chem., 2011, 36, 7407-7413.
[5]
(a) Zhang, Q.; Sun, J.; Zhang, F.; Yu, B. Eur. J. Org. Chem., 2010, 19, 3579-3582.
(b) Cai, S-T.; Xiang, S-H.; Zeng, J.; Gorityala, B.K.; Liu, X-W. Chem. Commun., 2011, 47, 8676-8678.
[6]
(a) Winterfeld, G.A.; Schmidt, R.R. Angew. Chem. Int. Ed., 2001, 40, 2654-2657.
(b) Winterfeld, G.A.; Khodair, A.I.; Schmidt, R.R. Eur. J. Org. Chem., 2003, 6, 1009-1021.
[7]
Reddy, B.G.; Vankar, Y.D. Tetrahedron Lett., 2003, 44, 4765-4767.
[8]
(a) Konstantinova, N.V.; Lavrova, M.F.; Nesterova, T.P.; Potapova, N.P.; Ponomarenko, V.I.; Rozynov, V.B.; Brazhnikova, M.G.; Lapchinskaya, O.A.; Sinyagina, O.P. Antibiotiki i Meditsinskaya Biotekhnologiya, 1985, 30, 729-732.
(b) Mori, T.; Ichiyanagi, T.; Kondo, H.; Tokunaga, K.; Oda, T.; Munakata, K. J. Antibiot., 1971, 24, 339-346.
[9]
Shylesh, S.; Schünemann, V.; Thiel, W.R. Angew. Chem. Int. Ed., 2010, 49, 3428-3459.
[10]
(a) Parella, R. Naveen; Kumar, A.; Babu, S.A. Tetrahedron Lett., 2013, 54, 1738-1742.
(b) Jiao, H.; Jiao, G.; Wang, J.S. ynth. React. Inorg. M, 2013, 43, 131-134.
[11]
(a) Santiago, C.C.; Lafuente, L.; Bravo, R.; Díaz, G.; Ponzinibbio, A. Tetrahedron Lett., 2017, 58, 3739-3742.
(b) Lafuente, L.; Díaz, G.; Bravo, R.; Ponzinibbio, A. Lett. Org. Chem., 2016, 13, 195-200.
(c) Díaz, G.; Ponzinibbio, A.; Bravo, R.D. Carbohydr. Res., 2014, 393, 23-25.
(d) Díaz, G.; Ponzinibbio, A.; Bravo, R.D. Top. Catal., 2012, 55, 644-648.
(e) Tasca, J.E.; Ponzinibbio, A.; Diaz, G.; Bravo, R.D.; Lavat, A.; González, M.G. Top. Catal., 2010, 53, 1087-1090.
(f) Ponzinibbio, A.; Colinas, P.A.; Lieberknecht, A.; Bravo, R.D. Lett. Org. Chem., 2006, 3, 459-462.
(g) Colinas, P.A.; Ponzinibbio, A.; Lieberknecht, A.; Bravo, R.D. Tetrahedron Lett., 2003, 44, 7985-7988.
[12]
Dharuman, S.; Gupta, P.; Kancharla, P.K.; Vankar, Y.D. J. Org. Chem., 2013, 78, 8442-8450.
[13]
Hofle, G.; Steglich, W.; Vorbrüggen, H. Angew. Chem. Int. Ed. Engl., 1978, 17, 569-583.
[14]
(a) Pradhan, K.; Paul, S.; Das, A.R. Catal. Sci. Technol., 2014, 4, 822-831.
(b) Pal, G.; Paul, S.; Das, A.R. New J. Chem., 2014, 38, 2787-2791, 5096.
[15]
Guo, J.; Ye, X-S. Molecules, 2010, 15, 7235-7265.
[16]
Das, J.; Schmidt, R.R. Eur. J. Org. Chem., 1998, 8, 1609-1613.
[17]
Astruc, D.; Lu, F.; Aranzaes, J.R. Angew. Chem. Int. Ed., 2005, 44, 7852-7872.
[18]
Nagaraj, P.; Ramesh, N.G. Tetrahedron, 2011, 67, 9322-9328.

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