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3
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PCT Int. Appl. WO 2006012440 A2
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Wang, P.; Stec, W.; Clark, J.; Chun, B.; Shi, J.; Du, J. PCT Int. Appl. WO 2006012440 A2, 2006.
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Wang, P.1
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PCT Int. Appl. WO 2006031725 A2
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Chun, B.; Wang, P. PCT Int. Appl. WO 2006031725 A2, 2006.
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Chun, B.1
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Ref. 2a,b Mayes, B. A.; Moussa, A. PCT Int. Appl. WO 2007075876 A2, 2007.
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6
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62849089456
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PCT Int. Appl. WO 2008045419 A1
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Axt, S. D.; Sarma, K.; Vitale, J.; Zhu, J.; Ross, B.; Rachakonda, S.; Jin, Q.; Chun, B. PCT Int. Appl. WO 2008045419 A1, 2008.
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Axt, S.D.1
Sarma, K.2
Vitale, J.3
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Ross, B.5
Rachakonda, S.6
Jin, Q.7
Chun, B.8
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Cedilote, M.; Cleary, T.; Iding, H.; Zhang, P. U.S. Pat. Appl. Publ. US 2008145901 A1, 2008.
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Cedilote, M.; Cleary, T.; Iding, H.; Zhang, P. U.S. Pat. Appl. Publ. US 2008145901 A1, 2008.
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Cedilote, M.; Cleary, T.; Zhang, P. U.S. Pat. Appl. Publ. US 2008177079 A1, 2008.
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9
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0001037653
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For example:. Bernrdi A., Beretta M.G., Colombo L., Gennari C., Poli G., and Scolastico C. J. Org. Chem. 50 (1985) 4442-4447
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Bernrdi, A.1
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Gennari, C.4
Poli, G.5
Scolastico, C.6
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10
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0346679509
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Kita, Y.1
Yasuda, H.2
Tamura, O.3
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Tamura, Y.6
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12
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0010626404
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Kita Y., Tamura O., Itoh F., Yasuda H., Kishino H., Ke Y.Y., and Tamura Y. J. Org. Chem. 53 (1988) 554-561
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Tamura, Y.7
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13
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0000679560
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Heathcock C.H., Young S.D., Hagen J.P., Pirrung M.C., White C.T., and Vanderveer D. J. Org. Chem. 45 (1980) 3846-3856
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White, C.T.5
Vanderveer, D.6
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16
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62849119942
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note
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To simplify this discussion, the term 'Z' or 'E' describes only the relationship between the methyl group and metallated oxygen, and the influence of the heavier fluorine and sulfur atoms on the nomenclature is ignored.
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18
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33845518355
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For examples:
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For examples:. Nagase R., Matsumoto N., Hosomi K., Hidashi T., Funakoshi S., Misaki T., and Tanabe Y. Org. Biomol. Chem. 5 (2007) 151-159
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21
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0026004927
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Annunziata R., Cinquini M., Cozzi F., Cozzi P.G., and Consolandi E. Tetrahedron 47 (1991) 7897-7910
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Annunziata, R.1
Cinquini, M.2
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Cozzi, P.G.4
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23
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0034746878
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Christlieb M., Davies J.E., Eames J., Hooley R., and Warren S. J. Chem. Soc., Perkin Trans. 1 (2001) 2983-2996
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26
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0022499278
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Patel D.V., VanMiddlesworth F., Donaubauer J., Gannett P., and Sih C.J. J. Am. Chem. Soc. 108 (1986) 4603-4604
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Sih, C.J.5
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29
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33748934565
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Ashley G.W., Burlingame M., Desai R., Fu H., Leaf T., Licari P.J., Tran C., Abbanat D., Bush K., and Macielag M. J. Antibiot. 59 (2006) 392-401
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Tran, C.7
Abbanat, D.8
Bush, K.9
Macielag, M.10
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36
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62849128517
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note
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3): δ 169.6, 169.4, 150.6, 142.8, 127.2, 125.9, 125.2, 116.0, 110.2, 86.7, 85.2, 18.1, 17.9.
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38
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62849121213
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Prepared following the literature procedure in Ref. 11
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Prepared following the literature procedure in Ref. 11
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39
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62849118202
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Prepared following the literature procedure in Ref. 12c.
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Prepared following the literature procedure in Ref. 12c.
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40
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62849107935
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Prepared following the literature procedure in Ref. 9
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Prepared following the literature procedure in Ref. 9
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41
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62849126222
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One possible cause for the low observed stereoselectivity in these reactions could be the formation of higher percentage of E-enolate favored by fluorine-metal interactions. Although fluorine-metal interactions were detected under certain circumstances e.g, Takemura, H, Kon, N, Kotoku, M, Nakashima, S, Otsuka, K, Yasutake, M, Shimyozu, T, Inazu, T. J. Org. Chem. 2001, 66, 2778; Barr, D, Hutton, K. B, Morris, J. H, Mulvey, R. E, Reed, D, Snaith, R. J. Chem. Soc, Chem. Commun. 1986, 127; Plenio, H. ChemBioChem 2004, 5, 650; and the references cited in these papers, no strong evidence for the existence of such interactions in α-fluoroenolates were reported in the literature. Some literature results might have indicated the lack of such interaction or the lack of influence of such an interaction on the E/Z ratio of enolates. For instance, 19F NMR of the enolates of N,N-dimethylfluoroacetamide indicated an almost 1:1 mixture of E/Z isomers even at -85 °C
-
19F NMR of the enolates of N,N-dimethylfluoroacetamide indicated an almost 1:1 mixture of E/Z isomers even at -85 °C (Welch, J. T.; Eswarakrishnan, S. J. Org. Chem. 1985, 50, 5403). Another example is that enolates 23 and 24 existed almost exclusively as Z-enolates under the reaction conditions (Refs. 15 and 17), indicating that the coordination between F-Li or F-Ti (if it exists) has little effect on the E/Z ratio.
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43
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62849092085
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note
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3): δ 4.98 (dq, J = 61, 8.5 Hz, 1H), 4.18 (t, J = 8.5 Hz, 2H), 1.70-1.60 (m, 2H), 1.57 (dd, J = 29.5, 8.5 Hz, 3H), 1.44-1.34 (m, 2H), 0.93 (t, J = 9 Hz, 3H).
-
-
-
-
44
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62849122701
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note
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3): δ 170.27, 170.09, 86.45, 85.00, 72.34, 37.93, 37.91, 19.92, 19.87, 18.61, 18.59, 18.47, 18.44, 18.29, 18.26, 13.83.
-
-
-
-
45
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62849124867
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note
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3): δ 170.51, 170.32, 86.43, 84.99, 78.21, 26.46, 26.42, 18.58, 18.40, 9.53.
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-
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47
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12344307017
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Aggarwal V.K., Astle C.J., Iding H., Wirz B., and Rogers-Evans M. Tetrahedron Lett. 46 (2005) 945-947
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Aggarwal, V.K.1
Astle, C.J.2
Iding, H.3
Wirz, B.4
Rogers-Evans, M.5
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49
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33751498908
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Schmid C.R., Bryant J.D., Dowlatzedah M., Philips J.L., Prather D.E., Schantz R.D., Sear N.L., and Vianco C.S. J. Org. Chem. 56 (1991) 4056-4058
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(1991)
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-
Schmid, C.R.1
Bryant, J.D.2
Dowlatzedah, M.3
Philips, J.L.4
Prather, D.E.5
Schantz, R.D.6
Sear, N.L.7
Vianco, C.S.8
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51
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62849091124
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CALB was a technical solution from BioCatalytics, Cat# SO L-101, Lot# CN02100.
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CALB was a technical solution from BioCatalytics, Cat# SO L-101, Lot# CN02100.
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