Copyright (c) 2014 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Evolution of Epoxides to Synthesize b-amino Alcohols: A Mini Review
Corresponding Author(s) : Yifeng Zhou
Asian Journal of Chemistry,
Vol. 26 No. 13 (2014): Vol 26 Issue 13
Abstract
The present short review about a great deal of researches have been dedicated to the development of the reaction (catalyzing the ring opening of epoxide with amines for the corresponding amino-alcohols) in recent years.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- L.E. Overman and L.A. Flippin, Tetrahedron Lett., 22, 195 (1981); doi:10.1016/0040-4039(81)80053-6.
- M. Santelli and J.-M. Pons, Lewis Acids and Selectivity in Organic Synthesis, CRC, Vol. 2 (1995).
- A. Corma and H. Garcia, ChemInform, 35, 606 (2004).
- G. Sundararajan, K. Vijayakrishna and B. Varghese, Tetrahedron Lett., 45, 8253 (2004); doi:10.1016/j.tetlet.2004.09.023.
- A.K. Chakraborti and A. Kondaskar, Tetrahedron Lett., 44, 8315 (2003); doi:10.1016/j.tetlet.2003.09.046.
- J. Augé and F. Leroy, Tetrahedron Lett., 37, 7715 (1996); doi:10.1016/0040-4039(96)01731-5.
- M. Chini, P. Crotti, L. Favero, F. Macchia and M. Pineschi, Tetrahedron Lett., 35, 433 (1994); doi:10.1016/0040-4039(94)85073-9.
- G. Sekar and V.K. Singh, J. Org. Chem., 64, 287 (1999); doi:10.1021/jo981196c.
- G. Mancilla, M. Femenía-Ríos, A.J. Macías-Sánchez and I.G. Collado, Tetrahedron, 64, 11732 (2008); doi:10.1016/j.tet.2008.09.099.
- I. Cepanec, M. Litvić, H. Mikuldaš, A. Bartolinčić and V. Vinković, Tetrahedron, 59, 2435 (2003); doi:10.1016/S0040-4020(03)00292-8.
- D.B.G. Williams and M. Lawton, Org. Biomol. Chem., 3, 3269 (2005); doi:10.1039/b508924g.
- D.B.G. Williams and M. Lawton, Tetrahedron Lett., 47, 6557 (2006); doi:10.1016/j.tetlet.2006.07.036.
- D.B.G. Williams and A. Cullen, J. Org. Chem., 74, 9509 (2009); doi:10.1021/jo9020437.
- A.T. Placzek, J.L. Donelson, R. Trivedi, R.A. Gibbs and S.K. De, Tetrahedron Lett., 46, 9029 (2005); doi:10.1016/j.tetlet.2005.10.106.
- A. Procopio, M. Gaspari, M. Nardi, M. Oliverio and O. Rosati, Tetrahedron Lett., 49, 2289 (2008); doi:10.1016/j.tetlet.2008.02.010.
- F. Carrée, R. Gil and J. Collin, Tetrahedron Lett., 45, 7749 (2004); doi:10.1016/j.tetlet.2004.08.048.
- L.R. Reddy, M.A. Reddy, N. Bhanumathi and K.R. Rao, Synthesis, 831 (2001); doi:10.1055/s-2001-13414.
- M. Maheswara, K.S.V.K. Rao and J.Y. Do, Tetrahedron Lett., 49, 1795 (2008); doi:10.1016/j.tetlet.2008.01.044.
- J. Wu, X.-L. Hou, L.-X. Dai, L.-J. Xia and M.-H. Tang, Tetrahedron Asymm., 9, 3431 (1998); doi:10.1016/S0957-4166(98)00358-9.
- F. Carrée, R. Gil and J. Collin, Org. Lett., 7, 1023 (2005); doi:10.1021/ol0475360.
- M. Martin, S. Bezzenine-Lafollée, R. Gil and J. Collin, Tetrahedron Asymm., 18, 2598 (2007); doi:10.1016/j.tetasy.2007.10.029.
- M. Martin, S. Bezzenine and J. Collin, Tetrahedron Asymm., 21, 1722 (2010); doi:10.1016/j.tetasy.2010.04.035.
- M. Martin, A. El Hellani, J. Yang, J. Collin and S. Bezzenine-Lafollée, J. Org. Chem., 76, 9801 (2011); doi:10.1021/jo2019015.
- K. Arai, S. Lucarini, M.M. Salter, K. Ohta, Y. Yamashita and S. Kobayashi, J. Am. Chem. Soc., 129, 8103 (2007); doi:10.1021/ja0708666.
- G. Bartoli, M. Bosco, A. Carlone, M. Locatelli, M. Massaccesi, P. Melchiorre and L. Sambri, Org. Lett., 6, 2173 (2004); doi:10.1021/ol049372t.
- G. Bartoli, M. Bosco, A. Carlone, M. Locatelli, P. Melchiorre and L. Sambri, Org. Lett., 7, 1983 (2005); doi:10.1021/ol050675c.
- B. Gao, Y. Wen, Z. Yang, X. Huang, X. Liu and X. Feng, Adv. Synth. Catal., 350, 385 (2008); doi:10.1002/adsc.200700474.
- J. Yadav, A. Antony, J. George and B.V. Subba Reddy, Eur. J. Org. Chem., 2010, 591 (2010); doi:10.1002/ejoc.200900895.
- J.R. Rodríguez and A. Navarro, Tetrahedron Lett., 45, 7495 (2004); doi:10.1016/j.tetlet.2004.08.010.
- K.J. Klabunde and R. Richards, Nanoscale Materials in Chemistry, Wiley Online Library (2001).
- B. Sreedhar, P. Radhika, B. Neelima and N. Hebalkar, J. Mol. Catal. Chem., 272, 159 (2007); doi:10.1016/j.molcata.2007.03.040.
- M.W. Robinson, A.M. Davies, I. Mabbett, T.E. Davies, D.C. Apperley, S.H. Taylor and A.E. Graham, J. Mol. Catal. Chem., 329, 57 (2010); doi:10.1016/j.molcata.2010.06.018.
- H. Kotsuki, T. Shimanouchi, M. Teraguchi, M. Kataoka, A. Tatsukawa and H. Nishizawa, Chem. Lett., 23, 2159 (1994); doi:10.1246/cl.1994.2159.
- M.W.C. Robinson, D.A. Timms, S.M. Williams and A.E. Graham, Tetrahedron Lett., 48, 6249 (2007); doi:10.1016/j.tetlet.2007.07.030.
- H.-F. Lu, L.-L. Sun, W.-J. Le, F.-F. Yang, J.-T. Zhou and Y.-H. Gao, Tetrahedron Lett., 53, 4267 (2012); doi:10.1016/j.tetlet.2012.05.079.
- D. Albanese, D. Landini and M. Penso, Tetrahedron, 53, 4787 (1997); doi:10.1016/S0040-4020(97)00162-2.
- M.M. Khodaei, A.R. Khosropour and K. Ghozati, Tetrahedron Lett., 45, 3525 (2004); doi:10.1016/j.tetlet.2004.02.139.
- D.P. Curran and L.H. Kuo, J. Org. Chem., 59, 3259 (1994); doi:10.1021/jo00091a007.
- D.P. Curran and L.H. Kuo, Tetrahedron Lett., 36, 6647 (1995); doi:10.1016/00404-0399(50)1394-W.
- M.S. Sigman and E.N. Jacobsen, J. Am. Chem. Soc., 120, 4901 (1998); doi:10.1021/ja980139y.
- P.R. Schreiner and A. Wittkopp, Org. Lett., 4, 217 (2002); doi:10.1021/ol017117s.
- S. Rampalli, S.S. Chaudhari and K.G. Akamanchi, Synthesis, 78 (2000); doi:10.1055/s-2000-6235.
- J.-D. Grunwaldt, R. Wandeler and A. Baiker, Catal. Rev., 45, 1 (2003); doi:10.1081/CR-120015738.
- M. Shi and Y. Chen, J. Fluor. Chem., 122, 219 (2003); doi:10.1016/S0022-1139(03)00083-6.
- B. Thirupathi, R. Srinivas, A.N. Prasad, J.P. Kumar and B.M. Reddy, Org. Process Res. Dev., 14, 1457 (2010); doi:10.1021/op1002177.
- N. Azizi and M.R. Saidi, Org. Lett., 7, 3649 (2005); doi:10.1021/ol051220q.
- N. Azizi and M.R. Saidi, Tetrahedron, 63, 888 (2007); doi:10.1016/j.tet.2006.11.045.
- M. Abdul Jalil and S.M. Masum, Tetrahedron Lett., 53, 3049 (2012); doi:10.1016/j.tetlet.2012.04.019.
- F. Fringuelli, F. Pizzo, S. Tortoioli and L. Vaccaro, J. Org. Chem., 69, 7745 (2004); doi:10.1021/jo049335f.
- R. Torregrosa, I.M. Pastor and M. Yus, Tetrahedron, 63, 469 (2007); doi:10.1016/j.tet.2006.10.055.
- L.-W. Xu, L. Li, C.-G. Xia and P.-Q. Zhao, Tetrahedron Lett., 45, 2435 (2004); doi:10.1016/j.tetlet.2004.01.042.
- S. Ishida, S. Suzuki, T. Hayano, H. Furuno and J. Inanaga, J. Alloy. Comp., 408-412, 441 (2006); doi:10.1016/j.jallcom.2004.12.079.
- R. Sheldon, Chem. Commun., 2399 (2001); doi:10.1039/b107270f.
- P. Wasserscheid and W. Keim, Angew. Chem., 39, 3772 (2000); doi:10.1002/1521-3773(20001103)39:21<3772::AID-ANIE3772>3.0.CO;2-5.
- M. Lakshmi Kantam, B. Neelima, C. Venkat Reddy and R. Chakravarti, Ind. Eng. Chem. Res., 46, 8614 (2007); doi:10.1021/ie070080g.
- A.K. Chakraborti, S. Rudrawar and A. Kondaskar, Org. Biomol. Chem., 2, 1277 (2004); doi:10.1039/b400588k.
- M. Maheswara, K.S.V.K. Rao and J.Y. Do, Tetrahedron Lett., 49, 1795 (2008); doi:10.1016/j.tetlet.2008.01.044.
- C. Zhang, J. Chen, X. Yu, X. Chen, H. Wu and J. Yu, Synth. Commun., 38, 1875 (2008); doi:10.1080/00397910801997405.
- M. Tajbakhsh, R. Hosseinzadeh, P. Rezaee and H. Alinezhad, J. Mex. Chem. Soc., 56, 402 (2012).
- J.P. Begue, D. Bonnet‐Delpon and B. Crousse, Synlett., 18 (2004); doi:10.1055/s-2003-44973.
- S. Khaksar, A. Heydari, M. Tajbakhsh and H.R. Bijanzadeh, J. Fluor. Chem., 131, 106 (2010);doi:10.1016/j.jfluchem.2009.10.003.
References
L.E. Overman and L.A. Flippin, Tetrahedron Lett., 22, 195 (1981); doi:10.1016/0040-4039(81)80053-6.
M. Santelli and J.-M. Pons, Lewis Acids and Selectivity in Organic Synthesis, CRC, Vol. 2 (1995).
A. Corma and H. Garcia, ChemInform, 35, 606 (2004).
G. Sundararajan, K. Vijayakrishna and B. Varghese, Tetrahedron Lett., 45, 8253 (2004); doi:10.1016/j.tetlet.2004.09.023.
A.K. Chakraborti and A. Kondaskar, Tetrahedron Lett., 44, 8315 (2003); doi:10.1016/j.tetlet.2003.09.046.
J. Augé and F. Leroy, Tetrahedron Lett., 37, 7715 (1996); doi:10.1016/0040-4039(96)01731-5.
M. Chini, P. Crotti, L. Favero, F. Macchia and M. Pineschi, Tetrahedron Lett., 35, 433 (1994); doi:10.1016/0040-4039(94)85073-9.
G. Sekar and V.K. Singh, J. Org. Chem., 64, 287 (1999); doi:10.1021/jo981196c.
G. Mancilla, M. Femenía-Ríos, A.J. Macías-Sánchez and I.G. Collado, Tetrahedron, 64, 11732 (2008); doi:10.1016/j.tet.2008.09.099.
I. Cepanec, M. Litvić, H. Mikuldaš, A. Bartolinčić and V. Vinković, Tetrahedron, 59, 2435 (2003); doi:10.1016/S0040-4020(03)00292-8.
D.B.G. Williams and M. Lawton, Org. Biomol. Chem., 3, 3269 (2005); doi:10.1039/b508924g.
D.B.G. Williams and M. Lawton, Tetrahedron Lett., 47, 6557 (2006); doi:10.1016/j.tetlet.2006.07.036.
D.B.G. Williams and A. Cullen, J. Org. Chem., 74, 9509 (2009); doi:10.1021/jo9020437.
A.T. Placzek, J.L. Donelson, R. Trivedi, R.A. Gibbs and S.K. De, Tetrahedron Lett., 46, 9029 (2005); doi:10.1016/j.tetlet.2005.10.106.
A. Procopio, M. Gaspari, M. Nardi, M. Oliverio and O. Rosati, Tetrahedron Lett., 49, 2289 (2008); doi:10.1016/j.tetlet.2008.02.010.
F. Carrée, R. Gil and J. Collin, Tetrahedron Lett., 45, 7749 (2004); doi:10.1016/j.tetlet.2004.08.048.
L.R. Reddy, M.A. Reddy, N. Bhanumathi and K.R. Rao, Synthesis, 831 (2001); doi:10.1055/s-2001-13414.
M. Maheswara, K.S.V.K. Rao and J.Y. Do, Tetrahedron Lett., 49, 1795 (2008); doi:10.1016/j.tetlet.2008.01.044.
J. Wu, X.-L. Hou, L.-X. Dai, L.-J. Xia and M.-H. Tang, Tetrahedron Asymm., 9, 3431 (1998); doi:10.1016/S0957-4166(98)00358-9.
F. Carrée, R. Gil and J. Collin, Org. Lett., 7, 1023 (2005); doi:10.1021/ol0475360.
M. Martin, S. Bezzenine-Lafollée, R. Gil and J. Collin, Tetrahedron Asymm., 18, 2598 (2007); doi:10.1016/j.tetasy.2007.10.029.
M. Martin, S. Bezzenine and J. Collin, Tetrahedron Asymm., 21, 1722 (2010); doi:10.1016/j.tetasy.2010.04.035.
M. Martin, A. El Hellani, J. Yang, J. Collin and S. Bezzenine-Lafollée, J. Org. Chem., 76, 9801 (2011); doi:10.1021/jo2019015.
K. Arai, S. Lucarini, M.M. Salter, K. Ohta, Y. Yamashita and S. Kobayashi, J. Am. Chem. Soc., 129, 8103 (2007); doi:10.1021/ja0708666.
G. Bartoli, M. Bosco, A. Carlone, M. Locatelli, M. Massaccesi, P. Melchiorre and L. Sambri, Org. Lett., 6, 2173 (2004); doi:10.1021/ol049372t.
G. Bartoli, M. Bosco, A. Carlone, M. Locatelli, P. Melchiorre and L. Sambri, Org. Lett., 7, 1983 (2005); doi:10.1021/ol050675c.
B. Gao, Y. Wen, Z. Yang, X. Huang, X. Liu and X. Feng, Adv. Synth. Catal., 350, 385 (2008); doi:10.1002/adsc.200700474.
J. Yadav, A. Antony, J. George and B.V. Subba Reddy, Eur. J. Org. Chem., 2010, 591 (2010); doi:10.1002/ejoc.200900895.
J.R. Rodríguez and A. Navarro, Tetrahedron Lett., 45, 7495 (2004); doi:10.1016/j.tetlet.2004.08.010.
K.J. Klabunde and R. Richards, Nanoscale Materials in Chemistry, Wiley Online Library (2001).
B. Sreedhar, P. Radhika, B. Neelima and N. Hebalkar, J. Mol. Catal. Chem., 272, 159 (2007); doi:10.1016/j.molcata.2007.03.040.
M.W. Robinson, A.M. Davies, I. Mabbett, T.E. Davies, D.C. Apperley, S.H. Taylor and A.E. Graham, J. Mol. Catal. Chem., 329, 57 (2010); doi:10.1016/j.molcata.2010.06.018.
H. Kotsuki, T. Shimanouchi, M. Teraguchi, M. Kataoka, A. Tatsukawa and H. Nishizawa, Chem. Lett., 23, 2159 (1994); doi:10.1246/cl.1994.2159.
M.W.C. Robinson, D.A. Timms, S.M. Williams and A.E. Graham, Tetrahedron Lett., 48, 6249 (2007); doi:10.1016/j.tetlet.2007.07.030.
H.-F. Lu, L.-L. Sun, W.-J. Le, F.-F. Yang, J.-T. Zhou and Y.-H. Gao, Tetrahedron Lett., 53, 4267 (2012); doi:10.1016/j.tetlet.2012.05.079.
D. Albanese, D. Landini and M. Penso, Tetrahedron, 53, 4787 (1997); doi:10.1016/S0040-4020(97)00162-2.
M.M. Khodaei, A.R. Khosropour and K. Ghozati, Tetrahedron Lett., 45, 3525 (2004); doi:10.1016/j.tetlet.2004.02.139.
D.P. Curran and L.H. Kuo, J. Org. Chem., 59, 3259 (1994); doi:10.1021/jo00091a007.
D.P. Curran and L.H. Kuo, Tetrahedron Lett., 36, 6647 (1995); doi:10.1016/00404-0399(50)1394-W.
M.S. Sigman and E.N. Jacobsen, J. Am. Chem. Soc., 120, 4901 (1998); doi:10.1021/ja980139y.
P.R. Schreiner and A. Wittkopp, Org. Lett., 4, 217 (2002); doi:10.1021/ol017117s.
S. Rampalli, S.S. Chaudhari and K.G. Akamanchi, Synthesis, 78 (2000); doi:10.1055/s-2000-6235.
J.-D. Grunwaldt, R. Wandeler and A. Baiker, Catal. Rev., 45, 1 (2003); doi:10.1081/CR-120015738.
M. Shi and Y. Chen, J. Fluor. Chem., 122, 219 (2003); doi:10.1016/S0022-1139(03)00083-6.
B. Thirupathi, R. Srinivas, A.N. Prasad, J.P. Kumar and B.M. Reddy, Org. Process Res. Dev., 14, 1457 (2010); doi:10.1021/op1002177.
N. Azizi and M.R. Saidi, Org. Lett., 7, 3649 (2005); doi:10.1021/ol051220q.
N. Azizi and M.R. Saidi, Tetrahedron, 63, 888 (2007); doi:10.1016/j.tet.2006.11.045.
M. Abdul Jalil and S.M. Masum, Tetrahedron Lett., 53, 3049 (2012); doi:10.1016/j.tetlet.2012.04.019.
F. Fringuelli, F. Pizzo, S. Tortoioli and L. Vaccaro, J. Org. Chem., 69, 7745 (2004); doi:10.1021/jo049335f.
R. Torregrosa, I.M. Pastor and M. Yus, Tetrahedron, 63, 469 (2007); doi:10.1016/j.tet.2006.10.055.
L.-W. Xu, L. Li, C.-G. Xia and P.-Q. Zhao, Tetrahedron Lett., 45, 2435 (2004); doi:10.1016/j.tetlet.2004.01.042.
S. Ishida, S. Suzuki, T. Hayano, H. Furuno and J. Inanaga, J. Alloy. Comp., 408-412, 441 (2006); doi:10.1016/j.jallcom.2004.12.079.
R. Sheldon, Chem. Commun., 2399 (2001); doi:10.1039/b107270f.
P. Wasserscheid and W. Keim, Angew. Chem., 39, 3772 (2000); doi:10.1002/1521-3773(20001103)39:21<3772::AID-ANIE3772>3.0.CO;2-5.
M. Lakshmi Kantam, B. Neelima, C. Venkat Reddy and R. Chakravarti, Ind. Eng. Chem. Res., 46, 8614 (2007); doi:10.1021/ie070080g.
A.K. Chakraborti, S. Rudrawar and A. Kondaskar, Org. Biomol. Chem., 2, 1277 (2004); doi:10.1039/b400588k.
M. Maheswara, K.S.V.K. Rao and J.Y. Do, Tetrahedron Lett., 49, 1795 (2008); doi:10.1016/j.tetlet.2008.01.044.
C. Zhang, J. Chen, X. Yu, X. Chen, H. Wu and J. Yu, Synth. Commun., 38, 1875 (2008); doi:10.1080/00397910801997405.
M. Tajbakhsh, R. Hosseinzadeh, P. Rezaee and H. Alinezhad, J. Mex. Chem. Soc., 56, 402 (2012).
J.P. Begue, D. Bonnet‐Delpon and B. Crousse, Synlett., 18 (2004); doi:10.1055/s-2003-44973.
S. Khaksar, A. Heydari, M. Tajbakhsh and H.R. Bijanzadeh, J. Fluor. Chem., 131, 106 (2010);doi:10.1016/j.jfluchem.2009.10.003.