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5
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34248653921
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For reviews, see:
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10
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34248674784
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Asymmetric synthesis of γ-amino acids mainly relied on diastereoselective reactions before Jacbosen's contribution (Ref. 8). For selected recent examples, see:
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11
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33750304716
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Capriati V., Degennaro L., Florio S., Luisi R., and Punzi P. Org. Lett. 8 (2006) 4803
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Capriati, V.1
Degennaro, L.2
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12
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25844449049
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Ueda M., Miyabe H., Sugino H., Miyata O., and Naito T. Angew. Chem., Int. Ed. 44 (2005) 6190
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Ueda, M.1
Miyabe, H.2
Sugino, H.3
Miyata, O.4
Naito, T.5
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15
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0033532930
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Appella D.H., Christianson L.A., Karle I.L., Powell D.R., and Gellman S.H. J. Am. Chem. Soc. 121 (1999) 6206
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Appella, D.H.1
Christianson, L.A.2
Karle, I.L.3
Powell, D.R.4
Gellman, S.H.5
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17
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23844530814
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Mita T., Fujimori I., Wada R., Wen J., Kanai M., and Shibasaki M. J. Am. Chem. Soc. 127 (2005) 11252
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Mita, T.1
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Wada, R.3
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Kanai, M.5
Shibasaki, M.6
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18
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21544444468
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For a review about the utility of chiral ligands 1 and 2, see:
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For a review about the utility of chiral ligands 1 and 2, see:. Kanai M., Kato N., Ichikawa E., and Shibasaki M. Synlett (2005) 1491
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(2005)
Synlett
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Kanai, M.1
Kato, N.2
Ichikawa, E.3
Shibasaki, M.4
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19
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34248641287
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note
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Addition of TFA slightly, but constantly, improved the enantioselectivity. ESIMS studies demonstrated that TFA is incorporated in the polymetallic complex. TFA likely bridges two Gd metals in the complex, and thus finely tunes the relative position of the two metals. In addition, TFA enhances the Lewis acidity of Gd in the catalyst.
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22
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34248673877
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Silverman, R. B.; Andruszkiewicz, R.; Yuen, P. W.; Sobieray, D. M.; Franklin, L. C.; Schwindt, M. A. U.S. Patent 5,563,175, 1996;
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23
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0042932780
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For recent catalytic enantioselective synthesis of pregabalin, see:
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For recent catalytic enantioselective synthesis of pregabalin, see:. Hoge G. J. Am. Chem. Soc. 125 (2003) 10219
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(2003)
J. Am. Chem. Soc.
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Hoge, G.1
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24
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2942635094
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Matsunaga S., Kinoshita T., Okada S., Harada S., and Shibasaki M. J. Am. Chem. Soc. 126 (2004) 7559
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J. Am. Chem. Soc.
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Matsunaga, S.1
Kinoshita, T.2
Okada, S.3
Harada, S.4
Shibasaki, M.5
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27
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33845944635
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Part of this work was reported in the previous communication, see:
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Part of this work was reported in the previous communication, see:. Fujimori I., Mita T., Maki K., Shiro M., Sato A., Furusho S., Kanai M., and Shibasaki M. J. Am. Chem. Soc. 128 (2006) 16438
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J. Am. Chem. Soc.
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Fujimori, I.1
Mita, T.2
Maki, K.3
Shiro, M.4
Sato, A.5
Furusho, S.6
Kanai, M.7
Shibasaki, M.8
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0035840992
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Yabu K., Masumoto S., Yamasaki S., Hamashima Y., Kanai M., Du W., Curran D.P., and Shibasaki M. J. Am. Chem. Soc. 123 (2001) 9908
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Yabu, K.1
Masumoto, S.2
Yamasaki, S.3
Hamashima, Y.4
Kanai, M.5
Du, W.6
Curran, D.P.7
Shibasaki, M.8
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Kato N., Mita T., Kanai M., Therrien B., Kawano M., Yamaguchi K., Danjo H., Sei Y., Sato A., Furusho S., and Shibasaki M. J. Am. Chem. Soc. 128 (2006) 6768
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Kato, N.1
Mita, T.2
Kanai, M.3
Therrien, B.4
Kawano, M.5
Yamaguchi, K.6
Danjo, H.7
Sei, Y.8
Sato, A.9
Furusho, S.10
Shibasaki, M.11
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An extreme example in which the 2:3 complex and the 4:5+μ-oxo crystal demonstrated contrasting catalyst function was the asymmetric Strecker reaction of ketoimines. These two asymmetric catalysts produced reversed enantioselectivity in an excellent level. See Ref. 14.
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Crystal structure of another polymetallic complex (La-1=6:8+2OH complex) described in Ref. 14 also contained this general module.
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35
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34248637194
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N2′-type reaction.
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Similar temperature dependency was also observed when using 18f and 18g as substrates.
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39
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34248664220
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The syn isomer should be generated from the kinetically produced anti isomer through catalyst-mediated epimerization of the benzylnitrile moiety.
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In the reaction of 18f, which has a relatively small size compared to 18g and 18i, the liberation of the product might be hindered due to the high coordinating ability of the product to the metal.
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41
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The protic additive activated the Gd-1=2:3 catalyst by forming a proton-containing complex, see:
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The protic additive activated the Gd-1=2:3 catalyst by forming a proton-containing complex, see:. Kato N., Suzuki M., Kanai M., and Shibasaki M. Tetrahedron Lett. 45 (2004) 3147
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(2004)
Tetrahedron Lett.
, vol.45
, pp. 3147
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Kato, N.1
Suzuki, M.2
Kanai, M.3
Shibasaki, M.4
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note
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Crystallographic data for the structural analysis have been deposited with the Cambridge Crystallographic Data Centre, CCDC No. 637203 for the Gd-4=3:4+2OH complex (Fig. 3b) and CCDC No. 637202 for 17 (Fig. 4).
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