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See, for examples:. Cole D.C. Tetrahedron 50 (1994) 9517-9582
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Fülöp, F.1
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37049076807
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See, for examples of stereoselective preparation of cyclic β-amino acids:
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See, for examples of stereoselective preparation of cyclic β-amino acids:. Davies S.G., Ichihara O., Lenoir I., and Walters I.A.S. J. Chem. Soc., Perkin Trans. 1 (1994) 1411-1415
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(1994)
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Davies, S.G.1
Ichihara, O.2
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Walters, I.A.S.4
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9
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0037471537
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Chippindale A.M., Davies S.G., Iwamoto K., Parkin R.M., Smethurst A.P., Smith A.D., and Rodriguez-Solla H. Tetrahedron 59 (2003) 3253-3265
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Chippindale, A.M.1
Davies, S.G.2
Iwamoto, K.3
Parkin, R.M.4
Smethurst, A.P.5
Smith, A.D.6
Rodriguez-Solla, H.7
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13
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17444396764
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Davies S.G., Diez D., Dominguez S.H., Garrido N.M., Kruchinin D., Price P.D., and Smith A.D. Org. Biomol. Chem. 3 (2005) 1284-1301
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Davies, S.G.1
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Kruchinin, D.5
Price, P.D.6
Smith, A.D.7
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15
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15444346262
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See, for examples of application of constrained β-aminoacids:
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See, for examples of application of constrained β-aminoacids:. Hayashi Y., Katade J., Harada T., Tachiki K., Takiguchi Y., Maramatsu M., Miyazaki H., Asari T., Okazaki T., Dato Y., Yasuda E., Tano M., Uno I., and Ojima I. J. Med. Chem. 41 (1998) 2345-2360
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Hayashi, Y.1
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Maramatsu, M.6
Miyazaki, H.7
Asari, T.8
Okazaki, T.9
Dato, Y.10
Yasuda, E.11
Tano, M.12
Uno, I.13
Ojima, I.14
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17
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0000780791
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Hibbs D.E., Hursthouse M.B., Jones I.G., Jones W., Malik K.M.A., and North M. J. Org. Chem. 63 (1998) 1496-1504
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Hibbs, D.E.1
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North, M.6
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0344731437
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Furet P., Garcia-Echeverria C., Gay B., Schoepfer J., Zeller M., and Rahuel J. J. Med. Chem. 42 (1999) 2358-2363
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Furet, P.1
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Sukopp M., Schwab R., Marinelli L., Biron E., Heller M., Varkondi E., Pap A., Novellino E., Kéri G., and Kessler H. J. Med. Chem. 48 (2005) 2916-2926
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Pap, A.7
Novellino, E.8
Kéri, G.9
Kessler, H.10
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25
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0001617895
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See, for examples:. Katagiri N., Ikatsuka H., Kaneko C., and Sera A. Tetrahedron Lett. 29 (1988) 5397-5401
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Katagiri, N.1
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4744348792
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Ohno M., Costanzi S., Sung Kim H., Kempeneers V., Vastmans K., Herdewijn P., Maddileti S., Gao Z.-G., Harden T.K., and Jacobson K.A. Bioorg. Med. Chem. 12 (2004) 5619-5630
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12444339842
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See, for recent example:
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See, for recent example:. Mitsumori S., Tsuri T., Honma T., Hiramatsu Y., Okada T., Hashizume H., Inagaki M., Arimura A., Yasui K., Asanuma F., Kishino J., and Ohtani M. J. Med. Chem. 46 (2003) 2436-2445
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Mitsumori, S.1
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Arimura, A.8
Yasui, K.9
Asanuma, F.10
Kishino, J.11
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35649015098
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Narisada, M.; Ohtani, M.; Watanabe, F.; Matsuura, T.; Hagishita, S.; Seno, K. Eur. Pat. Appl. EP 352083 B1, 1990; C.A. 1990, 113, 191362.
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Nohira, H.; Kikegara, K. Jpn. Kokai Tokyo Koko JP 06, 271, 765; C.A. 1995, 122, 132653n.
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Chang, L.L.1
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Schmidt, J.A.10
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See, for recent example:. Maechling S., Norman S.E., McKendrick J.E., Basra S., Köppner K., and Blechert S. Tetrahedron Lett. 47 (2006) 189-192
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(2006)
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See, for examples:. Kanerva L.T., Csomos P., Sundholm O., Bernath G., and Fülöp F. Tetrahedron: Asymmetry 7 (1996) 1705-1716
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Kanerva, L.T.1
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0033104471
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The nitro acrylate 6 was synthesized following the conditions described by Clive et al. for the preparation of the nitro acrylate ester of the (-)-8-phenylmenthol:
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The nitro acrylate 6 was synthesized following the conditions described by Clive et al. for the preparation of the nitro acrylate ester of the (-)-8-phenylmenthol:. Clive D.L.J., Bo Y., Selvakumar N. Tetrahedron 55 (1999) 3277-3290
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(1999)
Tetrahedron
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Clive, D.L.J.1
Bo, Y.2
Selvakumar, N.3
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35649024478
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note
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R (HPLC, column B, eluent I) 15.7 min (81%), 17.6 min (5%), 19.8 min (13%) and 24.6 min (1%)), the facial selectivity (94%) could be presumed.
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35648970284
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note
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13C spectra were observed for the different cycloadducts 7. For example 6-H and 5-H chemical shifts were respectively: (6.05 and 6.20 ppm (dd)) (81%), (6.03 and 6.24 ppm (dd)) (13%), (6.46 and 6.48 ppm (dd)) (5%) and (6.46 and 6.48 ppm (dd)) (∼1%).
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note
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2 = 0.1147 for 2627 reflections with I > 2σ(I). Details of the crystal structure (excluding structure factors) have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 659166. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(0)-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk].
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note
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Neutral alumina was kept in an oven at 120 °C and cooled in a dessicator with silica gel before usage.
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50
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35649004624
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note
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Compound 5 contains about 5-7% of the compound (S)-1 (HPLC analysis) as inevitable hydrolysis of the ester bond during the Henry reaction, that was transformed in an OMesyl derivative in the following step providing the nitroacrylate (S)-6.
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