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1
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78049409183
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Enantioenriched allylic esters are ubiquitous intermediates in the synthesis of complex molecules. Selected recent examples include the following
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Enantioenriched allylic esters are ubiquitous intermediates in the synthesis of complex molecules. Selected recent examples include the following:
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2
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76249122299
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Shimizu, Y., Shi, S.-L., Usuda, H., Kanai, M., and Shibasaki, M. Angew. Chem., Int. Ed. 2010, 49, 1103-1106
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78049369363
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For a comprehensive review of the synthesis of allylic alcohols, see
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For a comprehensive review of the synthesis of allylic alcohols, see
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6
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64549126511
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In;, Ed.; Thieme: Stuttgart
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Hodgson, D. M. and Humphreys, P. G. In Science of Synthesis: Houben-Weyl Methods of Molecular Transformations; Clayden, J. P., Ed.; Thieme: Stuttgart, 2007; Vol. 36, pp 583 - 665.
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7
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78049368579
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Enzymatic kinetic resolution
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Enzymatic kinetic resolution
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8
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13344277260
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78049375823
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Palladium-catalyzed kinetic resolution
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Palladium-catalyzed kinetic resolution
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13
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73349131689
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Ebner, D. C., Bagdanoff, J. T., Ferreira, E. M., McFadden, R. M., Caspi, D. D., Trend, R. M., and Stoltz, B. M. Chem.-Eur. J. 2009, 15, 12978-12992
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Corey, E.J.1
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78049414444
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A novel catalytic asymmetric approach involving Cu-catalyzed catalytic asymmetric allylic alkylation was described recently
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A novel catalytic asymmetric approach involving Cu-catalyzed catalytic asymmetric allylic alkylation was described recently
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23
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44649088181
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Geurts, K., Fletcher, S. P., van Zijl, A. W., Minnaard, A. J., and Feringa, B. L. Pure Appl. Chem. 2008, 80, 1025-1037
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26
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78049405577
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For comprehensive reviews see
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For comprehensive reviews see
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29
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78049385985
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Direct palladium-catalyzed allylic C-H oxidation to provide 3-acyloxy-1-alkenes in modest enantioselectivity has been reported by the White group
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Direct palladium-catalyzed allylic C-H oxidation to provide 3-acyloxy-1-alkenes in modest enantioselectivity has been reported by the White group
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30
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52049103427
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López, F.1
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Evans, P. A., Leahy, D. K., and Slieker, L. M. Tetrahedron: Asymmetry 2003, 14, 3613-3618
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Evans, P.A.1
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Onitsuka, K., Okuda, H., and Sasai, H. Angew. Chem., Int. Ed. 2008, 47, 1454-1457
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Onitsuka, K.1
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40
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78049360897
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For a recent review of enantioselective allylation reactions, see
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For a recent review of enantioselective allylation reactions, see
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41
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38049017956
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Lu, Z. and Ma, S. Angew. Chem., Int. Ed. 2008, 47, 258-297
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Lu, Z.1
Ma, S.2
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78049357221
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For a recent review, see
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For a recent review, see
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43
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33846933027
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Helmchen, G.1
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33749006910
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Lyothier, I.1
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Anderson, C. E., Kirsch, S. F., Overman, L. E., Richards, C. J., and Watson, M. P. Org. Synth. 2007, 84, 148-155
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Org. Synth.
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Anderson, C.E.1
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85026878649
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Anderson, C. E., Overman, L. E., Richards, C. J., Watson, M. P., and White, N. S. Org. Synth. 2007, 84, 139-147
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Anderson, C.E.1
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78049377270
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J. Am. Chem. Soc. 2010, http://dx.doi.org/10.1021/ja106688j, following paper in this issue
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Cannon, J., Kirsch, S. F., Overman, L. E., and Sneddon, H. F. J. Am. Chem. Soc. 2010, 132, http://dx.doi.org/10.1021/ja106688j, following paper in this issue.
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Cannon, J.1
Kirsch, S.F.2
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52
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78049368296
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Cationic complexes were generated from chloride-bridged dimer precursors by pretreatment at room temperature with 4 equiv of the silver salt specified in Figure 1
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Cationic complexes were generated from chloride-bridged dimer precursors by pretreatment at room temperature with 4 equiv of the silver salt specified in Figure 1.
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53
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78049372617
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A negative sign before the % ee indicates that ent - 4b was produced in excess
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A negative sign before the % ee indicates that ent-4b was produced in excess.
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54
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0000653605
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Calter, M., Hollis, T. K., Overman, L. E., Ziller, J., and Zipp, G. G. J. Org. Chem. 1997, 62, 1449-1456
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Calter, M.1
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Zipp, G.G.5
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0002768578
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Sokolov, V. I., Troitskaya, L. L., and Reutov, J. J. Organomet. Chem. 1977, 133, C28-C30
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Sokolov, V.I.1
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8644276255
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Kirsch, S. F., Overman, L. E., and Watson, M. P. J. Org. Chem. 2004, 69, 8101-8104
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Kirsch, S.F.1
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73349129970
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Olson, A. C., Overman, L. E., Sneddon, H. F., and Ziller, J. W. Adv. Synth. Catal. 2009, 351, 3186-3192
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Olson, A.C.1
Overman, L.E.2
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Ziller, J.W.4
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60
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78049390816
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a = 12.8; calculated using Advanced Chemistry Development (ACD/Labs) Software, version 8.14
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a = 12.8; calculated using Advanced Chemistry Development (ACD/Labs) Software, version 8.14.
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61
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0041350419
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Overman, L. E., Owen, C. E., and Pavan, M. M. Org. Lett. 2003, 5, 1809-1812
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(2003)
Org. Lett.
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Overman, L.E.1
Owen, C.E.2
Pavan, M.M.3
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63
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78049376833
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Under identical conditions, allylic trichloroacetamide is not detected in the corresponding reaction of (Z)-imidate 3b
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Under identical conditions, allylic trichloroacetamide is not detected in the corresponding reaction of (Z)-imidate 3b.
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64
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78049387302
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This result is not surprising in light of the rapid interconversion of catalysts 2 and 14 in the presence of acetic acid
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This result is not surprising in light of the rapid interconversion of catalysts 2 and 14 in the presence of acetic acid.
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66
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0026526050
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Martin, V. S., Ode, J. M., Palazón, J. M., and Soler, M. A. Tetrahedron: Asymmetry 1992, 3, 573-580
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(1992)
Tetrahedron: Asymmetry
, vol.3
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Martin, V.S.1
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Palazón, J.M.3
Soler, M.A.4
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68
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78049385076
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None of the reactions reported in Table 4 were homogeneous
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None of the reactions reported in Table 4 were homogeneous.
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69
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78049403735
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In the absence of catalyst 2, reaction of 3e with o -chlorobenzoic acid provided ∼20% conversion to the linear o -chlorobenzoate ester after 24 h
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In the absence of catalyst 2, reaction of 3e with o -chlorobenzoic acid provided ∼20% conversion to the linear o -chlorobenzoate ester after 24 h.
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70
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34247531301
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Watson, M. P., Overman, L. E., and Bergman, R. G. J. Am. Chem. Soc. 2007, 129, 5031-5044
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J. Am. Chem. Soc.
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Watson, M.P.1
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Oishi, T., Ando, K., Inomiya, K., Sato, H., Iida, M., and Chida, N. Bull. Chem. Soc. Jpn. 2002, 75, 1927-1947
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2 (2) at room temperature. However, this reaction is low yielding because the catalyst becomes poisoned, presumably from the formation of a minor byproduct
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2 (2) at room temperature. However, this reaction is low yielding because the catalyst becomes poisoned, presumably from the formation of a minor byproduct.
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