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1
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0000496226
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For representative examples, see:. Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds), Springer-Verlag, Berlin, Germany
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For representative examples, see:. Jacobsen E.N., and Wu M.H. In: Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds). Comprehensive Asymmetric Catalysis I-III Vol. 3 (1999), Springer-Verlag, Berlin, Germany 1306-1326
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(1999)
Comprehensive Asymmetric Catalysis I-III
, vol.3
, pp. 1306-1326
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-
Jacobsen, E.N.1
Wu, M.H.2
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3
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2542530041
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In the design of sulfonamide-based MMP inhibitors, typically, the biaryl ether potion was attached to the sulfonyl group instead of on the nitrogen atom. Few exceptions, see:
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In the design of sulfonamide-based MMP inhibitors, typically, the biaryl ether potion was attached to the sulfonyl group instead of on the nitrogen atom. Few exceptions, see:. Cherney R.J., Mo R., Meyer D.T., Hardman K.D., Liu R.-Q., Covington M.B., Qian M., Wasserman Z.R., Christ D.D., Trzaskos J.M., Newton R.C., and Decicco C.P. J. Med. Chem. 47 (2004) 2981-2983
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(2004)
J. Med. Chem.
, vol.47
, pp. 2981-2983
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-
Cherney, R.J.1
Mo, R.2
Meyer, D.T.3
Hardman, K.D.4
Liu, R.-Q.5
Covington, M.B.6
Qian, M.7
Wasserman, Z.R.8
Christ, D.D.9
Trzaskos, J.M.10
Newton, R.C.11
Decicco, C.P.12
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4
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20144387816
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Kim S.-H., Pudzianowski A.T., Leavitt K.J., Barbosa J., McDonnell P.A., Metzler W.J., Rankin B.M., Liu R., Vaccaro W., and Pitts W. Bioorg. Med. Chem. Lett. 15 (2005) 1101-1106
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(2005)
Bioorg. Med. Chem. Lett.
, vol.15
, pp. 1101-1106
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Kim, S.-H.1
Pudzianowski, A.T.2
Leavitt, K.J.3
Barbosa, J.4
McDonnell, P.A.5
Metzler, W.J.6
Rankin, B.M.7
Liu, R.8
Vaccaro, W.9
Pitts, W.10
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6
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33646527790
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Cleator E., Sheen F.J., Bio M.M., Brands K.M.J., Davies A.J., and Dolling U.H. Tetrahedron Lett. 47 (2006) 4245-4248
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(2006)
Tetrahedron Lett.
, vol.47
, pp. 4245-4248
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Cleator, E.1
Sheen, F.J.2
Bio, M.M.3
Brands, K.M.J.4
Davies, A.J.5
Dolling, U.H.6
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7
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1842763607
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An example on intramolecular cyclization using trifluoroacetic acid, see:
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An example on intramolecular cyclization using trifluoroacetic acid, see:. Goujon J.-Y., Zammattio F., Chrětien J.M., and Beaudet I. Tetrahedron 60 (2004) 4037-4049
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(2004)
Tetrahedron
, vol.60
, pp. 4037-4049
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Goujon, J.-Y.1
Zammattio, F.2
Chrětien, J.M.3
Beaudet, I.4
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8
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33745215114
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Representative examples on microwave assisted epoxide opening with other nucleophiles, see:
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Representative examples on microwave assisted epoxide opening with other nucleophiles, see:. Kureshy R.I., Singh S., Khan N.H., Abdi S.R., Agrawal S., Mayani V.J., and Jasra R.V. Tetrahedron Lett. 47 (2006) 5277-5279
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(2006)
Tetrahedron Lett.
, vol.47
, pp. 5277-5279
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Kureshy, R.I.1
Singh, S.2
Khan, N.H.3
Abdi, S.R.4
Agrawal, S.5
Mayani, V.J.6
Jasra, R.V.7
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11
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33947601467
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Desai H., D'Souza B.R., Foether D., Johnson B.F., and Lindsay H.A. Synthesis (2007) 902-910
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(2007)
Synthesis
, pp. 902-910
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Desai, H.1
D'Souza, B.R.2
Foether, D.3
Johnson, B.F.4
Lindsay, H.A.5
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12
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37649002057
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note
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6S: C, 56.98; H, 5.58; N, 3.69. Found: C, 56.88; H, 5.54; N, 3.61.
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-
-
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13
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28244465504
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1H NMR analysis of the crude mixture. The ring opening of styrene oxide usually associates with the regioselectivity issue. Some examples see: and Refs. 3a and 5d
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1H NMR analysis of the crude mixture. The ring opening of styrene oxide usually associates with the regioselectivity issue. Some examples see:. Placzek A.T., Donelson J.L., Trivedi R., Gibbs R.A., and De S.K. Tetrahedron Lett. 46 (2005) 9029-9034 and Refs. 3a and 5d
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(2005)
Tetrahedron Lett.
, vol.46
, pp. 9029-9034
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Placzek, A.T.1
Donelson, J.L.2
Trivedi, R.3
Gibbs, R.A.4
De, S.K.5
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14
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37649006759
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note
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Under the same irradiation using DMF as the solvent, 55% isolated yield of 13 was obtained. Under a thermal condition (90 °C, 24 h) or a microwave condition (DMF, 120 °C, 40 min), low conversion (<15%) was observed. In addition, the microwave condition (DMSO, 180 °C, 90 min) was also able to promote the ring opening of 5f with N-(4-methylphenyl)methyl 2-propanesulfonamide 19 to afford rac-20 (60%){A figure is presented}.
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15
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15644374838
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The condition was adopted from
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The condition was adopted from. MacPherson L.J., Bayburt E.K., Capparelli M.P., Carroll B.J., Goldstein R., Justice M.R., Zhu L., Hu S., Melton R.A., Fryer L., Goldberg R.L., Doughty J.R., Spirito S., Blancuzzi V., Wilson D., O'Byrne E.M., Ganu V., and Parker D.T. J. Med. Chem. 40 (1997) 2525-2532
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(1997)
J. Med. Chem.
, vol.40
, pp. 2525-2532
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-
MacPherson, L.J.1
Bayburt, E.K.2
Capparelli, M.P.3
Carroll, B.J.4
Goldstein, R.5
Justice, M.R.6
Zhu, L.7
Hu, S.8
Melton, R.A.9
Fryer, L.10
Goldberg, R.L.11
Doughty, J.R.12
Spirito, S.13
Blancuzzi, V.14
Wilson, D.15
O'Byrne, E.M.16
Ganu, V.17
Parker, D.T.18
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17
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4644254781
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Uenishi J., Hamada M., Aburatani S., Matsui K., Yonemitsu O., and Tsukube H. J. Org. Chem. 69 (2004) 6781-6789
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(2004)
J. Org. Chem.
, vol.69
, pp. 6781-6789
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Uenishi, J.1
Hamada, M.2
Aburatani, S.3
Matsui, K.4
Yonemitsu, O.5
Tsukube, H.6
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