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1
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34249716952
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For general reviews on 1,3-dipolar cycloadditions, see:
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2
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0003916113
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Padwa A., and Pearson W.H. (Eds), Wiley, New York, NY
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In: Padwa A., and Pearson W.H. (Eds). Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Towards Heterocycles and Natural Products (2003), Wiley, New York, NY
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(2003)
Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Towards Heterocycles and Natural Products
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6
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34249717492
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Review:
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8
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25844444557
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Palomo C., Oiarbide M., Arceo E., García J.M., López R., González A., and Linden A. Angew. Chem., Int. Ed. 44 (2005) 6187
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Palomo, C.1
Oiarbide, M.2
Arceo, E.3
García, J.M.4
López, R.5
González, A.6
Linden, A.7
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12
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20544472149
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Sibi M.P., Ma Z., Itoh K., Prabagaran N., and Jasperse C.P. Org. Lett. 7 (2005) 2349
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Sibi, M.P.1
Ma, Z.2
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Prabagaran, N.4
Jasperse, C.P.5
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33751250813
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Ashizawa T., Ohtsuki N., Miura T., Ohya M., Shinozaki T., Ikeno T., and Yamada T. Heterocycles 68 (2006) 1801
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Heterocycles
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Ashizawa, T.1
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Shinozaki, T.5
Ikeno, T.6
Yamada, T.7
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Kitagaki S., Anada M., Kataoka O., Matsuno K., Umeda C., Watanabe N., and Hashimoto S. J. Am. Chem. Soc. 121 (1999) 1417
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Watanabe, N.6
Hashimoto, S.7
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25
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34249665099
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Reviews:
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30
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0037112719
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Gothelf A.S., Gothelf K.V., Hazell R.G., and Jørgensen K.A. Angew. Chem., Int. Ed. 41 (2002) 4236
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Angew. Chem., Int. Ed.
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Gothelf, A.S.1
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0347916937
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Oderaotoshi Y., Cheng W., Fujitomi S., Kasano Y., Minakata S., and Komatsu M. Org. Lett. 5 (2003) 5043
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Oderaotoshi, Y.1
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33746290157
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Yan X.-X., Peng Q., Zhang Y., Zhang K., Hong W., Hou X.-L., and Wu Y.-D. Angew. Chem., Int. Ed. 45 (2006) 1979
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Angew. Chem., Int. Ed.
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Yan, X.-X.1
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Wu, Y.-D.7
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39
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33845320520
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For a recent review on chiral ferrocene ligands in asymmetric catalysis, see:
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For a recent review on chiral ferrocene ligands in asymmetric catalysis, see:. Gómez Arrayás R., Adrio J., and Carretero J.C. Angew. Chem., Int. Ed. 45 (2006) 7674
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Angew. Chem., Int. Ed.
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Gómez Arrayás, R.1
Adrio, J.2
Carretero, J.C.3
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40
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0036977771
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Priego J., García Mancheño O., Cabrera S., Gómez Arrayás R., Llamas T., and Carretero J.C. Chem. Commun. (2002) 2512
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Chem. Commun.
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Priego, J.1
García Mancheño, O.2
Cabrera, S.3
Gómez Arrayás, R.4
Llamas, T.5
Carretero, J.C.6
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41
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0037414501
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García Mancheño O., Priego J., Cabrera S., Gómez Arrayás R., Llamas T., and Carretero J.C. J. Org. Chem. 68 (2003) 3679
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J. Org. Chem.
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García Mancheño, O.1
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Gómez Arrayás, R.4
Llamas, T.5
Carretero, J.C.6
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48
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0029010218
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For the synthesis of aryl- and alkylimino esters, see:
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For the synthesis of aryl- and alkylimino esters, see:. Cooper D.M., Grigg R., Hargreaves S., Kennewell P., and Redpath J. Tetrahedron 51 (1995) 7791
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(1995)
Tetrahedron
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Cooper, D.M.1
Grigg, R.2
Hargreaves, S.3
Kennewell, P.4
Redpath, J.5
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49
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34249735517
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note
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For trans alkenes, endo refers to the cycloadduct with the electron-withdrawing group at C-4 and the aromatic groups at C-5 are cis to each other. Similarly, exo refers to the cycloadduct where the same groups are trans to each other.
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50
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34249673553
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For 1,3-dipolar cycloadditions of nitrones with acroleins, see:
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51
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12144286166
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Carmona D., Lamata M.P., Viguri F., Rodríguez R., Oro L.A., Balana A.I., Lahoz F.J., Tejero T., Merino P., Franco S., and Montesa I. J. Am. Chem. Soc. 126 (2004) 2716
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J. Am. Chem. Soc.
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Carmona, D.1
Lamata, M.P.2
Viguri, F.3
Rodríguez, R.4
Oro, L.A.5
Balana, A.I.6
Lahoz, F.J.7
Tejero, T.8
Merino, P.9
Franco, S.10
Montesa, I.11
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53
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21044456157
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Zubia A., Mendoza L., Vivanco S., Aldaba E., Carrascal T., Lecea B., Arrieta A., Zimmerman T., Vidal-Vanaclocha F., and Cossío F.P. Angew. Chem., Int. Ed. 44 (2005) 2903
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Angew. Chem., Int. Ed.
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Zubia, A.1
Mendoza, L.2
Vivanco, S.3
Aldaba, E.4
Carrascal, T.5
Lecea, B.6
Arrieta, A.7
Zimmerman, T.8
Vidal-Vanaclocha, F.9
Cossío, F.P.10
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54
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37049089476
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Amornraksa K., Grigg R., Guranatne H.Q.N., Kemp J., and Sridharan V. J. Chem. Soc., Perkin Trans. 1 (1987) 2285
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(1987)
J. Chem. Soc., Perkin Trans. 1
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Amornraksa, K.1
Grigg, R.2
Guranatne, H.Q.N.3
Kemp, J.4
Sridharan, V.5
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55
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0034725364
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Vivanco S., Lecea B., Arrieta A., Prieto P., Morao I., Linden A., and Cossío F.P. J. Am. Chem. Soc. 122 (2000) 6078
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Vivanco, S.1
Lecea, B.2
Arrieta, A.3
Prieto, P.4
Morao, I.5
Linden, A.6
Cossío, F.P.7
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56
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0001001548
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A similar behaviour was observed in related cycloadducts. See for example:
-
A similar behaviour was observed in related cycloadducts. See for example:. Woller P.B., and Cromwell N.H. J. Org. Chem. 35 (1970) 888
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(1970)
J. Org. Chem.
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Woller, P.B.1
Cromwell, N.H.2
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57
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34249661291
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note
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Due to the low stability of 5g and 5h, they have to be immediately used after preparation.
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-
-
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58
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34249656455
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note
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4/rac-1a (5 mol %) only yielded endo adduct.
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-
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64
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84873055189
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Wiley, New York, NY pp 76-87 and references therein
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Hehre W.J., Radom L., Schleyer P.v.R., and Pople J.A. Ab initio Molecular Orbital Theory (1986), Wiley, New York, NY pp 76-87 and references therein
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(1986)
Ab initio Molecular Orbital Theory
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Hehre, W.J.1
Radom, L.2
Schleyer, P.v.R.3
Pople, J.A.4
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15744375697
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Gaussian, Wallingford, CT
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Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery Jr. J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C., and Pople J.A. Gaussian 03, Revision C.02 (2004), Gaussian, Wallingford, CT
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(2004)
Gaussian 03, Revision C.02
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Frisch, M.J.1
Trucks, G.W.2
Schlegel, H.B.3
Scuseria, G.E.4
Robb, M.A.5
Cheeseman, J.R.6
Montgomery Jr., J.A.7
Vreven, T.8
Kudin, K.N.9
Burant, J.C.10
Millam, J.M.11
Iyengar, S.S.12
Tomasi, J.13
Barone, V.14
Mennucci, B.15
Cossi, M.16
Scalmani, G.17
Rega, N.18
Petersson, G.A.19
Nakatsuji, H.20
Hada, M.21
Ehara, M.22
Toyota, K.23
Fukuda, R.24
Hasegawa, J.25
Ishida, M.26
Nakajima, T.27
Honda, Y.28
Kitao, O.29
Nakai, H.30
Klene, M.31
Li, X.32
Knox, J.E.33
Hratchian, H.P.34
Cross, J.B.35
Bakken, V.36
Adamo, C.37
Jaramillo, J.38
Gomperts, R.39
Stratmann, R.E.40
Yazyev, O.41
Austin, A.J.42
Cammi, R.43
Pomelli, C.44
Ochterski, J.W.45
Ayala, P.Y.46
Morokuma, K.47
Voth, G.A.48
Salvador, P.49
Dannenberg, J.J.50
Zakrzewski, V.G.51
Dapprich, S.52
Daniels, A.D.53
Strain, M.C.54
Farkas, O.55
Malick, D.K.56
Rabuck, A.D.57
Raghavachari, K.58
Foresman, J.B.59
Ortiz, J.V.60
Cui, Q.61
Baboul, A.G.62
Clifford, S.63
Cioslowski, J.64
Stefanov, B.B.65
Liu, G.66
Liashenko, A.67
Piskorz, P.68
Komaromi, I.69
Martin, R.L.70
Fox, D.J.71
Keith, T.72
Al-Laham, M.A.73
Peng, C.Y.74
Nanayakkara, A.75
Challacombe, M.76
Gill, P.M.W.77
Johnson, B.78
Chen, W.79
Wong, M.W.80
Gonzalez, C.81
Pople, J.A.82
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