-
2
-
-
0000569942
-
-
Leading references: a) H. Steinhagen, M. Reggelin, G. Helmchen, Angew. Chem. 1997, 109, 2199-2202; Angew. Chem. Int. Ed. Engl. 1997, 36, 2108-2110; b) D. L. Romero, E. L. Fritzen, Tetrahedron Lett. 1997, 38, 8659-8662; c) reveiws: G. Consiglio, R. M. Waymouth, Chem. Rev. 1989, 89, 257-276; d) C. G. Frost, J. Howarth, J. M. J. Williams, Tetrahedron: Asymmetry 1992, 3, 1089-1122; e) B. M. Trost, D. L. Van Vranken, Chem. Rev. 1996, 96, 395-422.
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Steinhagen, H.1
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3
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0030853206
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Leading references: a) H. Steinhagen, M. Reggelin, G. Helmchen, Angew. Chem. 1997, 109, 2199-2202; Angew. Chem. Int. Ed. Engl. 1997, 36, 2108-2110; b) D. L. Romero, E. L. Fritzen, Tetrahedron Lett. 1997, 38, 8659-8662; c) reveiws: G. Consiglio, R. M. Waymouth, Chem. Rev. 1989, 89, 257-276; d) C. G. Frost, J. Howarth, J. M. J. Williams, Tetrahedron: Asymmetry 1992, 3, 1089-1122; e) B. M. Trost, D. L. Van Vranken, Chem. Rev. 1996, 96, 395-422.
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4
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0030786789
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Leading references: a) H. Steinhagen, M. Reggelin, G. Helmchen, Angew. Chem. 1997, 109, 2199-2202; Angew. Chem. Int. Ed. Engl. 1997, 36, 2108-2110; b) D. L. Romero, E. L. Fritzen, Tetrahedron Lett. 1997, 38, 8659-8662; c) reveiws: G. Consiglio, R. M. Waymouth, Chem. Rev. 1989, 89, 257-276; d) C. G. Frost, J. Howarth, J. M. J. Williams, Tetrahedron: Asymmetry 1992, 3, 1089-1122; e) B. M. Trost, D. L. Van Vranken, Chem. Rev. 1996, 96, 395-422.
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Romero, D.L.1
Fritzen, E.L.2
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5
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0024302311
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Leading references: a) H. Steinhagen, M. Reggelin, G. Helmchen, Angew. Chem. 1997, 109, 2199-2202; Angew. Chem. Int. Ed. Engl. 1997, 36, 2108-2110; b) D. L. Romero, E. L. Fritzen, Tetrahedron Lett. 1997, 38, 8659-8662; c) reveiws: G. Consiglio, R. M. Waymouth, Chem. Rev. 1989, 89, 257-276; d) C. G. Frost, J. Howarth, J. M. J. Williams, Tetrahedron: Asymmetry 1992, 3, 1089-1122; e) B. M. Trost, D. L. Van Vranken, Chem. Rev. 1996, 96, 395-422.
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Waymouth, R.M.2
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6
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0026722772
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Leading references: a) H. Steinhagen, M. Reggelin, G. Helmchen, Angew. Chem. 1997, 109, 2199-2202; Angew. Chem. Int. Ed. Engl. 1997, 36, 2108-2110; b) D. L. Romero, E. L. Fritzen, Tetrahedron Lett. 1997, 38, 8659-8662; c) reveiws: G. Consiglio, R. M. Waymouth, Chem. Rev. 1989, 89, 257-276; d) C. G. Frost, J. Howarth, J. M. J. Williams, Tetrahedron: Asymmetry 1992, 3, 1089-1122; e) B. M. Trost, D. L. Van Vranken, Chem. Rev. 1996, 96, 395-422.
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Frost, C.G.1
Howarth, J.2
Williams, J.M.J.3
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7
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6844254916
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Leading references: a) H. Steinhagen, M. Reggelin, G. Helmchen, Angew. Chem. 1997, 109, 2199-2202; Angew. Chem. Int. Ed. Engl. 1997, 36, 2108-2110; b) D. L. Romero, E. L. Fritzen, Tetrahedron Lett. 1997, 38, 8659-8662; c) reveiws: G. Consiglio, R. M. Waymouth, Chem. Rev. 1989, 89, 257-276; d) C. G. Frost, J. Howarth, J. M. J. Williams, Tetrahedron: Asymmetry 1992, 3, 1089-1122; e) B. M. Trost, D. L. Van Vranken, Chem. Rev. 1996, 96, 395-422.
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Trost, B.M.1
Van Vranken, D.L.2
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10
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84987263015
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Reaction of 1,3-diaryl propenyl acetates with non-racemic chiral Pd complexes is independent of the ee of the substrate : P. von Matt, G. C. Lloyd-Jones, A. B. E. Minidis, A. Pfaltz, L. Macko, M. Neuburger, M. Zehnder, H. Rüegger, P. S. Pregosin, Helv. Chim. Acta. 1995, 78, 265-284.
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Pfaltz, A.4
Macko, L.5
Neuburger, M.6
Zehnder, M.7
Rüegger, H.8
Pregosin, P.S.9
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11
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3743053643
-
-
note
-
II catalyst (see for example reference [7]) to effect 1,3-allylic isomerisation (final α/γ ≈ 0.9).
-
-
-
-
12
-
-
0000224924
-
-
II can effect formal 1,3-sigmatropic rearrangement of allylic esters: a) L. E. Overman, F. M. Knoll, Tetrahedron Lett. 1979, 4, 321-324; b) T. G. Schenk, B. Bosnich, J. Am. Chem. Soc. 1985, 107, 2058-2066
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Tetrahedron Lett.
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Overman, L.E.1
Knoll, F.M.2
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13
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0001244429
-
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II can effect formal 1,3-sigmatropic rearrangement of allylic esters: a) L. E. Overman, F. M. Knoll, Tetrahedron Lett. 1979, 4, 321-324; b) T. G. Schenk, B. Bosnich, J. Am. Chem. Soc. 1985, 107, 2058-2066
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Schenk, T.G.1
Bosnich, B.2
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14
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0003887404
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Harper and Row, NY
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The magnitude of a SKIE usually reflects differences in C-hybridisation between ground state and transition state at the reacting centres: T. H. Lowry, K. S. Richardson, Mechanism and Theory in Organic Chemistry, 3rd ed., Harper and Row, NY, 1987, pp. 232-244.
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(1987)
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Lowry, T.H.1
Richardson, K.S.2
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15
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0006038886
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-
Isotopic perturbation of resonance may also be involved, see for example a) D. A. Forsyth, M. M. MacConnell, J. Am. Chem. Soc. 1983, 105, 5920-5921; b) J. R. Wesener, H. Günther, Tetrahedron Lett. 1982, 23, 2845-2848.
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Forsyth, D.A.1
MacConnell, M.M.2
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0006038361
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Isotopic perturbation of resonance may also be involved, see for example a) D. A. Forsyth, M. M. MacConnell, J. Am. Chem. Soc. 1983, 105, 5920-5921; b) J. R. Wesener, H. Günther, Tetrahedron Lett. 1982, 23, 2845-2848.
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Wesener, J.R.1
Günther, H.2
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20
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0000005129
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d) B. M. Trost, M. Lautens, M.-H. Hung, C. S. Carmichael, J. Am. Chem. Soc. 1984, 106, 7641-7643;
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Trost, B.M.1
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Hung, M.-H.3
Carmichael, C.S.4
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0000327101
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e) B. M. Trost, G. B. Tometzki, M.-H. Hung, J. Am. Chem. Soc. 1987, 109, 2176-2177;
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Hung, M.-H.3
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23
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0032507004
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-
For highly enantioselectivc catalysis by related Mo complexes bearing ligands related to 3 see: B. M. Trost, I. Hachiya, J. Am. Chem. Soc. 1998, 120, 1104-1105; see also D. Dvořák, I. Starý, P. Koćovský, J. Am. Chem. Soc. 1995, 117, 6130-6131.
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Trost, B.M.1
Hachiya, I.2
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24
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0040553338
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For highly enantioselectivc catalysis by related Mo complexes bearing ligands related to 3 see: B. M. Trost, I. Hachiya, J. Am. Chem. Soc. 1998, 120, 1104-1105; see also D. Dvořák, I. Starý, P. Koćovský, J. Am. Chem. Soc. 1995, 117, 6130-6131.
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Dvořák, D.1
Starý, I.2
Koćovský, P.3
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25
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0000569942
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-
Later transition states have been suggested for asymmetric allylic alkylation, see for example: a) H. Steinhagen, M. Reggelin, G. Helmchen, Angew. Chem. 1997, 109, 2199-2202, Angew. Chem. Int. Ed. Engl. 1997, 36, 2108-2110; b) J. M. Brown, D. I. Hulmes, P. J. Guiry, Tetrahedron 1994, 50, 4493-4506.
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Steinhagen, H.1
Reggelin, M.2
Helmchen, G.3
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26
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0030853206
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Later transition states have been suggested for asymmetric allylic alkylation, see for example: a) H. Steinhagen, M. Reggelin, G. Helmchen, Angew. Chem. 1997, 109, 2199-2202, Angew. Chem. Int. Ed. Engl. 1997, 36, 2108-2110; b) J. M. Brown, D. I. Hulmes, P. J. Guiry, Tetrahedron 1994, 50, 4493-4506.
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-
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27
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0028232428
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Later transition states have been suggested for asymmetric allylic alkylation, see for example: a) H. Steinhagen, M. Reggelin, G. Helmchen, Angew. Chem. 1997, 109, 2199-2202, Angew. Chem. Int. Ed. Engl. 1997, 36, 2108-2110; b) J. M. Brown, D. I. Hulmes, P. J. Guiry, Tetrahedron 1994, 50, 4493-4506.
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Brown, J.M.1
Hulmes, D.I.2
Guiry, P.J.3
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28
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0002615576
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Greater ligand bite-angle is suggested to result in later transition states: M. Kranenburg, P. C. J. Kamer, P. W. N. M. van Leeuwen, Eur. J. Inorg. Chem. 1998, 1, 25-27.
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Van Leeuwen, P.W.N.M.3
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29
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33845379753
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Early transition states have also been suggested: P. B. Mackenzie, J. Whelan, B. Bosnich, J. Am. Chem. Soc. 1985, 107, 2046-2054.
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Mackenzie, P.B.1
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0001651521
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R. Prétôt, A. Pfaltz, Angew. Chem. 1998, 110, 337-339, Angew. Chem. Int. Ed. 1998, 37, 323-325.
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Pfaltz, A.2
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0032536559
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R. Prétôt, A. Pfaltz, Angew. Chem. 1998, 110, 337-339, Angew. Chem. Int. Ed. 1998, 37, 323-325.
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32
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0000385149
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supplimentary material
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These conditions follow those reported earlier, except that racemic (±)-3 instead of enantiomerically pure (S,S)- or (R,R)-3 isused; B. M. Trost, R. C. Bunt, J. Am. Chem. Soc. 1996, 118, 235-236, supplimentary material.
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J. Am. Chem. Soc.
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Trost, B.M.1
Bunt, R.C.2
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33
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0032515420
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-
After turnover ceased, the concentrations of α-6 and γ-6 were invariant and thus the reactions are irreversible. Dimethylmalonate can act as a nucleofuge in allylic alkylation - although usually under more forcing conditions, see for example: a) B. M. Trost, R. C. Bunt, J. Am. Chem. Soc. 1998, 120, 70-79; b) H. Bricout, J.-F. Carpentier, A. Mortreux, Tetrahedron Lett. 1997, 38, 1053-1056.
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Trost, B.M.1
Bunt, R.C.2
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34
-
-
0031562044
-
-
After turnover ceased, the concentrations of α-6 and γ-6 were invariant and thus the reactions are irreversible. Dimethylmalonate can act as a nucleofuge in allylic alkylation - although usually under more forcing conditions, see for example: a) B. M. Trost, R. C. Bunt, J. Am. Chem. Soc. 1998, 120, 70-79; b) H. Bricout, J.-F. Carpentier, A. Mortreux, Tetrahedron Lett. 1997, 38, 1053-1056.
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Bricout, H.1
Carpentier, J.-F.2
Mortreux, A.3
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35
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0003887404
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a) T. H. Lowry, K. S. Richardson, Mechanism and Theory in Organic Chemistry, 3rd ed., Harper and Row, NY, 1987, pp. 341-349;
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Mechanism and Theory in Organic Chemistry, 3rd Ed.
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Lowry, T.H.1
Richardson, K.S.2
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37
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1542482127
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c) S. S. Kantner, K. Humski, H. L. Goering, J. Am. Chem. Soc. 1982, 104, 1693-1697.
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Kantner, S.S.1
Humski, K.2
Goering, H.L.3
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38
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3743127397
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18O-(±)-5b
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18O-(±)-5b.
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40
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0031016772
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U. Burckhardt, M. Baumann, A. Togni, Tetrahedron: Asymmetry 1997, 8, 155-159.
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Burckhardt, U.1
Baumann, M.2
Togni, A.3
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41
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0001704975
-
-
The halide is postulated to do this by acceleration of exo and endo rotamer equilibration in intermediate 1,3-diphenyl allyl Pd-(PN) complexes by one or more of the following: i) Berry pseudorotation in a pentacoordinate intermediate, ii) π-σ-π allylic equilibrium or iii) N-dissociation-rotation-coordination - see, for example, A. Gogoll, J. Örnebro, H. Grennberg, J. E. Bäckvall, J. Am. Chem. Soc. 1994, 116, 3631-3632.
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Gogoll, A.1
Örnebro, J.2
Grennberg, H.3
Bäckvall, J.E.4
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43
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0001507379
-
-
For substrates and nucleofuges that behave differently see: a) M. E. Krafft, A. M. Wilson, Z. Fu, M. J. Proctor, O. A. Dasse, J. Org. Chem. 1998, 63, 1748-1749; b) C. N. Farthing, P. Kočovský, J. Am. Chem. Soc. 1998, 120, 6661-6672; c) I. Starý, P. Kočovský, J. Am. Chem. Soc. 1989, 111, 4981-4982; d) I. Starý, J. Zajíček, P. Kočovský, Tetrahedron, 1992, 48, 7229-7250
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Krafft, M.E.1
Wilson, A.M.2
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Proctor, M.J.4
Dasse, O.A.5
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44
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2642670293
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For substrates and nucleofuges that behave differently see: a) M. E. Krafft, A. M. Wilson, Z. Fu, M. J. Proctor, O. A. Dasse, J. Org. Chem. 1998, 63, 1748-1749; b) C. N. Farthing, P. Kočovský, J. Am. Chem. Soc. 1998, 120, 6661-6672; c) I. Starý, P. Kočovský, J. Am. Chem. Soc. 1989, 111, 4981-4982; d) I. Starý, J. Zajíček, P. Kočovský, Tetrahedron, 1992, 48, 7229-7250
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Farthing, C.N.1
Kočovský, P.2
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0000491494
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For substrates and nucleofuges that behave differently see: a) M. E. Krafft, A. M. Wilson, Z. Fu, M. J. Proctor, O. A. Dasse, J. Org. Chem. 1998, 63, 1748-1749; b) C. N. Farthing, P. Kočovský, J. Am. Chem. Soc. 1998, 120, 6661-6672; c) I. Starý, P. Kočovský, J. Am. Chem. Soc. 1989, 111, 4981-4982; d) I. Starý, J. Zajíček, P. Kočovský, Tetrahedron, 1992, 48, 7229-7250
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0026782148
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For substrates and nucleofuges that behave differently see: a) M. E. Krafft, A. M. Wilson, Z. Fu, M. J. Proctor, O. A. Dasse, J. Org. Chem. 1998, 63, 1748-1749; b) C. N. Farthing, P. Kočovský, J. Am. Chem. Soc. 1998, 120, 6661-6672; c) I. Starý, P. Kočovský, J. Am. Chem. Soc. 1989, 111, 4981-4982; d) I. Starý, J. Zajíček, P. Kočovský, Tetrahedron, 1992, 48, 7229-7250
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Starý, I.1
Zajíček, J.2
Kočovský, P.3
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47
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3743110501
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-
note
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3 signals.
-
-
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48
-
-
3743079437
-
-
note
-
1H). For all reactions except Table 2, entry 6, the ratio of [α-(S)-6 + γ-(R)-6] to [α-(R)-6+γ- (S)-6] was, within experimental error, 1:1 as predicted by a stereospecific mechanism.
-
-
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49
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0032579177
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a) H.-J. Gais, H. Eichelmann, N. Spalthoff, F. Gerhards, M. Frank, G. Raabe, Tetrahedron; Asymmetry 1998, 9, 235-248;
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Gais, H.-J.1
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Spalthoff, N.3
Gerhards, F.4
Frank, M.5
Raabe, G.6
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51
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0002140218
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m)]. Subsequent experiments with enantiomerically pure 3 and (±)-4a-d have confirmed that kinetic resolution occurs, and also that catalytic quantities of chloride ion can substantially accelerate reaction: G. C. Lloyd-Jones, S. C. Stephen, Chem. Commun. 1998, 2321-2322.
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Lloyd-Jones, G.C.1
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0027408256
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N. W. Alcock, J. M. Brown, D. I. Hulmes, Tetrahedron: Asymmetry 1993, 4, 743-756.
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Alcock, N.W.1
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a) T. Hayashi, M. Kawatsura, Y. Uozumi, J. Am. Chem. Soc. 1998, 120, 1681-1687;
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Hayashi, T.1
Kawatsura, M.2
Uozumi, Y.3
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56
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3743137335
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-
note
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Very recently, it has been suggested that the ligand may act as a 'PP(O)′ ligand by one of the carbonyl oxygens acting as a third donor through a van der Waals interaction with the Pd: B. M. Trost, H. Hagelin, unpublished results cited in reference [43].
-
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58
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0000146695
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a) P. von Matt, A. Pfaltz, Angew. Chem. 1993, 105, 614-615; Angew. Chem. Int. Ed. Engl. 1993, 32, 566-567;
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a) P. von Matt, A. Pfaltz, Angew. Chem. 1993, 105, 614-615; Angew. Chem. Int. Ed. Engl. 1993, 32, 566-567;
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61
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G. J. Dawson, C. G. Frost, J. M. J. Williams, Tetrahedron Lett. 1993, 34, 3149-3150.
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Dawson, G.J.1
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Williams, J.M.J.3
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62
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0000390005
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note
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2-Pd-π-[C(1)=C(2)]- C(3) alkene complex, respectively. For a discussion see: A. Pfaltz, Acta Chem. Scand. 1996, 50, 189-194 and references therein; see also references: [12a] and [12b].
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64
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0006989799
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0 catalysed) to give the enantiomeric product to C-allylation.
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68
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84987584194
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2]- cyclopentanol, 0% de.
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