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2
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a) T. D. Machajewski, C.-H. Wong, Angew. Chem. 2000, 112, 1406-1430; Angew. Chem. Int. Ed. 2000, 39, 1352-1375;
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Machajewski, T.D.1
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3
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a) T. D. Machajewski, C.-H. Wong, Angew. Chem. 2000, 112, 1406-1430; Angew. Chem. Int. Ed. 2000, 39, 1352-1375;
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6
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4544340769
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(Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, chap. 27
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A. Yanagisawa in Comprehensive Asymmetric Catalysis (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 2000, chap. 27.
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Comprehensive Asymmetric Catalysis
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Yanagisawa, A.1
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8
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0141631780
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b) M. E. Jung, B. Hoffmann, B. Rausch, J.-M. Contreras, Org. Lett. 2003, 5, 3159-3161.
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9
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0348241047
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J. W. Bode, N. Fraefel, D. Muri, E. M. Carreira, Angew. Chem. 2001, 113, 2128-2131; Angew. Chem. Int. Ed. 2001, 40, 2082-2085.
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Bode, J.W.1
Fraefel, N.2
Muri, D.3
Carreira, E.M.4
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10
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0001386311
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J. W. Bode, N. Fraefel, D. Muri, E. M. Carreira, Angew. Chem. 2001, 113, 2128-2131; Angew. Chem. Int. Ed. 2001, 40, 2082-2085.
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11
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0003497902
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(Eds.: S. Kobayashi, K. A. Jørgensen), Wiley-VCH, Weinheim, chap. 4
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a) K. A. Jørgensen in Cycloaddition Reactions in Organic Synthesis (Eds.: S. Kobayashi, K. A. Jørgensen), Wiley-VCH, Weinheim, 2001, chap. 4, pp. 151-185;
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Jørgensen, K.A.1
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12
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0013059152
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b) K. Gademann, D. E. Chavez, E. N. Jacobsen, Angew. Chem. 2002, 114, 3185-3187; Angew. Chem. Int. Ed. 2002, 41, 3059-3061.
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Angew. Chem.
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Gademann, K.1
Chavez, D.E.2
Jacobsen, E.N.3
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13
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0037118895
-
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b) K. Gademann, D. E. Chavez, E. N. Jacobsen, Angew. Chem. 2002, 114, 3185-3187; Angew. Chem. Int. Ed. 2002, 41, 3059-3061.
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Angew. Chem. Int. Ed.
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-
-
14
-
-
4544325444
-
-
note
-
3(2π)] cycloaddition.
-
-
-
-
15
-
-
0000171437
-
-
a) H.M.R. Hoffmann, Angew. Chem. 1973, 85, 877-894; Angew. Chem. Int. Ed. Engl. 1973, 12, 819-835;
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Angew. Chem.
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Hoffmann, H.M.R.1
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16
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84981911736
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a) H.M.R. Hoffmann, Angew. Chem. 1973, 85, 877-894; Angew. Chem. Int. Ed. Engl. 1973, 12, 819-835;
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Angew. Chem. Int. Ed. Engl.
, vol.12
, pp. 819-835
-
-
-
18
-
-
0002683218
-
-
c) H. M. R. Hoffmann, Angew. Chem. 1984, 96, 29-48; Angew. Chem. Int. Ed. Engl. 1984, 23, 1-19;
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Angew. Chem.
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Hoffmann, H.M.R.1
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19
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2242421018
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c) H. M. R. Hoffmann, Angew. Chem. 1984, 96, 29-48; Angew. Chem. Int. Ed. Engl. 1984, 23, 1-19;
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Angew. Chem. Int. Ed. Engl.
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-
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20
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0001523555
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d) J. Mann, Tetrahedron 1986, 42, 4611-4659;
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(1986)
Tetrahedron
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Mann, J.1
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28
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33746442416
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-
For an excellent review on enantioselective desymmetrizations, see M. C. Willis, J. Chem. Soc. Perkin Trans. 1 1999, 1765-1784; see also M. Anstiss, J. A. Holland, A. Nelson, J. R. Titchmarsh, Synlett 2003, 1213-1220.
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J. Chem. Soc. Perkin Trans. 1
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Willis, M.C.1
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29
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0038729536
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For an excellent review on enantioselective desymmetrizations, see M. C. Willis, J. Chem. Soc. Perkin Trans. 1 1999, 1765-1784; see also M. Anstiss, J. A. Holland, A. Nelson, J. R. Titchmarsh, Synlett 2003, 1213-1220.
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Synlett
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Anstiss, M.1
Holland, J.A.2
Nelson, A.3
Titchmarsh, J.R.4
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31
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0001719148
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H. M. R. Hoffmann, D. Wagner, R. Wartchow, Chem. Ber. 1990, 123, 2131-2139.
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Chem. Ber.
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Hoffmann, H.M.R.1
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Wartchow, R.3
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32
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0029824320
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M. Lautens, R. Aspiotis, J. Colucci, J. Am. Chem. Soc. 1996,118, 10930-10931.
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Lautens, M.1
Aspiotis, R.2
Colucci, J.3
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33
-
-
0001892927
-
-
aa = chair-shaped ring with two axial substituents: J. G. Vinter, H. M. R. Hoffmann, J. Am. Chem. Soc. 1974, 96, 5466-5478; see also J. G. Vinter, H. M. R. Hoffmann, J. Am. Chem. Soc. 1973, 95, 3051-3053.
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Vinter, J.G.1
Hoffmann, H.M.R.2
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34
-
-
0013537193
-
-
aa = chair-shaped ring with two axial substituents: J. G. Vinter, H. M. R. Hoffmann, J. Am. Chem. Soc. 1974, 96, 5466-5478; see also J. G. Vinter, H. M. R. Hoffmann, J. Am. Chem. Soc. 1973, 95, 3051-3053.
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J. Am. Chem. Soc.
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Vinter, J.G.1
Hoffmann, H.M.R.2
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37
-
-
4544334160
-
-
For a related approach, see E. Torres, Y. Chen, I. C. Kim, P. L. Fuchs, Angew. Chem. 2003, 115, 3232-3239; Angew. Chem. Int. Ed. 2003, 42, 3124-3131.
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Torres, E.1
Chen, Y.2
Kim, I.C.3
Fuchs, P.L.4
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38
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0042812113
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-
For a related approach, see E. Torres, Y. Chen, I. C. Kim, P. L. Fuchs, Angew. Chem. 2003, 115, 3232-3239; Angew. Chem. Int. Ed. 2003, 42, 3124-3131.
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Angew. Chem. Int. Ed.
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40
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0033607704
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b) M. Lautens, O. de Frutos, T. A. Stammers, Tetrahedron Lett. 1999, 40, 8317-8321.
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Lautens, M.1
De Frutos, O.2
Stammers, T.A.3
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41
-
-
4544265529
-
-
note
-
N2′openings of 8-oxabicyclo[3.2.1]oct-6-en-3-ones the approach of the incoming nucleophile syn to the leaving ether bridge is sterically and electronically favored.
-
-
-
-
43
-
-
0025374135
-
-
For [4+3] cycloadditions from silyl enol ethers of 1,1-dimethoxyacetone by action of Lewis acids, see a) D. H. Murray, K. F. Albizati, Tetrahedron Lett. 1990, 31, 4109;
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Tetrahedron Lett.
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Murray, D.H.1
Albizati, K.F.2
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45
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0001244484
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C. B. W. Stark, U. Eggert, H. M. R. Hoffmann, Angew. Chem. 1998, 110, 1337-1339; Angew. Chem. Int. Ed. 1998, 37, 1266-1268.
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Angew. Chem.
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Stark, C.B.W.1
Eggert, U.2
Hoffmann, H.M.R.3
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46
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0032543083
-
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C. B. W. Stark, U. Eggert, H. M. R. Hoffmann, Angew. Chem. 1998, 110, 1337-1339; Angew. Chem. Int. Ed. 1998, 37, 1266-1268.
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-
-
-
47
-
-
4544358682
-
-
note
-
2-symmetric acetals were not successful and necessitated more forcing conditions for cleavage of the acetal group.
-
-
-
-
48
-
-
4544367448
-
-
note
-
The methyl substituent of the chiral auxiliary in the diastereomeric transition state leading to the minor product 17 points toward the silyl tether.
-
-
-
-
49
-
-
0034681560
-
-
C. B. W. Stark, S. Pierau, R. Wartchow, H. M. R. Hoffmann, Chem. Eur. J. 2000, 6, 684-691.
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Stark, C.B.W.1
Pierau, S.2
Wartchow, R.3
Hoffmann, H.M.R.4
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50
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0000792432
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H. Beck, C. B. W. Stark, H. M. R. Hoffmann, Org. Lett. 2000, 2, 883-886.
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Org. Lett.
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Beck, H.1
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Hoffmann, H.M.R.3
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51
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0035984562
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K. J. Hale, M. G. Hummersone, S. Manaviazar, M. Frigerio, Nat. Prod. Rep. 2002, 19, 413-453.
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Nat. Prod. Rep.
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Hale, K.J.1
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Manaviazar, S.3
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52
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4544238614
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PhD thesis, Universität Hannover
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C. B. W. Stark, PhD thesis, Universität Hannover, 2000.
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Stark, C.B.W.1
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53
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84989528856
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PhD thesis, Universität Hannover
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S. Proemmel, PhD thesis, Universität Hannover, 2001. For earlier results employing racemic 8-oxabicyclo[3.2.1]oct-6-en-3-ones, see a) J. Reinecke, H. M. R. Hoffmann, Chem. Eur. J. 1995, 1, 368-372;
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Proemmel, S.1
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54
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84989528856
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S. Proemmel, PhD thesis, Universität Hannover, 2001. For earlier results employing racemic 8-oxabicyclo[3.2.1]oct-6-en-3-ones, see a) J. Reinecke, H. M. R. Hoffmann, Chem. Eur. J. 1995, 1, 368-372;
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Reinecke, J.1
Hoffmann, H.M.R.2
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55
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0032487971
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b) J. Wittenberg, W. Beil, H. M. R. Hoffmann, Tetrahedron Lett. 1998, 39, 8259-8262;
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Tetrahedron Lett.
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Wittenberg, J.1
Beil, W.2
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56
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0037194302
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c) S. Proemmel, R. Wartchow, H. M. R. Hoffmann, Tetrahedron 2002, 58, 6199-6206.
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Proemmel, S.1
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Hoffmann, H.M.R.3
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57
-
-
0000627417
-
-
For early work on the trialkylsilylmethylene terminator in [4+3] cycloadditions, see a) H. M. R. Hoffmann, U. Eggert, U. Gibbels, K. Giesel, O. Koch, R. Lies, I. Rabe, Tetrahedron 1988, 44, 3899-3918;
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Hoffmann, H.M.R.1
Eggert, U.2
Gibbels, U.3
Giesel, K.4
Koch, O.5
Lies, R.6
Rabe, I.7
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58
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0040619523
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b) H. M. R. Hoffmann, R. Henning, O. R. Lalko, Angew. Chem. 1982, 94, 464-465; Angew. Chem. Int. Ed. Engl. 1982, 21, 442;
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Hoffmann, H.M.R.1
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59
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84981928084
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b) H. M. R. Hoffmann, R. Henning, O. R. Lalko, Angew. Chem. 1982, 94, 464-465; Angew. Chem. Int. Ed. Engl. 1982, 21, 442;
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Angew. Chem. Int. Ed. Engl.
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62
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0012879582
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e) H. M. R. Hoffmann, A. Weber, R. J. Giguere, Chem. Ber. 1984, 117, 3325-3329.
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Chem. Ber.
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Hoffmann, H.M.R.1
Weber, A.2
Giguere, R.J.3
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63
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a) M. Harmata, D. E. Jones, M. Kahraman, U. Sharma, C. L. Barnes, Tetrahedron Lett. 1999, 40, 1831-1834;
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Tetrahedron Lett.
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Harmata, M.1
Jones, D.E.2
Kahraman, M.3
Sharma, U.4
Barnes, C.L.5
-
65
-
-
4544336020
-
-
note
-
A mechanistic model to explain the observed facial selectivity has not yet been proposed.
-
-
-
-
66
-
-
0001474567
-
-
S. Y. Cho, J. C. Lee, J. K. Cha, J. Org. Chem. 1999, 64, 3394-3395; see also: ref. [12].
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Cho, S.Y.1
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0034822714
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a) H. Xiong, R. P. Hsung, C. R. Berry, C. Rameshkumar, J. Am. Chem. Soc. 2001, 123, 7174-7175;
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Xiong, H.1
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68
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0037154775
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b) C. Rameshkumar, H. Xiong, M. R. Tracey, C. R. Berry, L. J. Yao, R. P. Hsung, J. Org. Chem. 2002, 67, 1339-1345.
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Rameshkumar, C.1
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0037124403
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H. Xiong, R. P. Hsung, L. Shen, J. M. Hahn, Tetrahedron Lett. 2002, 43, 4449-4453.
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Xiong, H.1
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Hahn, J.M.4
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70
-
-
0034600250
-
-
The intermediate oxyvinyliminium cation 35 is closely related to the iminium species involved in organocatalytic Diels-Alder and 1,3-dipolar cycloadditions developed by the MacMillan research group: a) K. A. Ahrendt, C. J. Borths, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 4243-4244;
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Ahrendt, K.A.1
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b) W. S. Jen, J. J. M. Wiener, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 9874-9875.
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Jen, W.S.1
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75
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4544268761
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note
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s)-p-toluenesulfinate.
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76
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M. Harmata, S. K. Ghosh, X. Hong, S. Wacharasindhu, P. Kirchhoefer, J. Am. Chem. Soc. 2003, 125, 2058-2059.
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Harmata, M.1
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77
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H. Kim, C. Ziani-Cherif, J. Oh, J. K. Cha, J. Org. Chem. 1995, 60, 792-793.
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Kim, H.1
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78
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84926469654
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J. Oh, C. Ziani-Cherif, J.-R. Choi, J. K. Cha, Org. Synth. 2002, 78, 212-219; see also: H. M. R. Hoffmann in Encyclopedia of Reagents for Organic Synthesis, Vol. 7 (Ed.: L. A. Paquette), Wiley, New York, 1995, pp. 4591-4593.
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Org. Synth.
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Oh, J.1
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84926469654
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M. Lautens, S. Ma, A. Yee, Tetrahedron Lett. 1995, 36, 4185-4188.
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Lautens, M.1
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0031026331
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Kaku et al. reported in 1997 that enzymatic desymmetrization of the bisacetate derived from meso-configured diol 51 to give monoacetate 52 in 72% yield with 96% ee is feasible when Pseudomonas fluorescence lipase (PFL) is employed: H. Kaku, M. Tanaka, Y. Norimine, Y. Miyashita, H. Suemune, K. Sakai, Tetrahedron: Asymmetry 1997, 8, 195-201.
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82
-
-
4544377092
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-
note
-
The parent oxabicyclic ketone meso-54 can be synthesized on a 0.5 mole scale from 1,1,3,3-tetrabromoacetone and furan employing the triethylborate-Zn/Cu procedure[53c] to yield 31-35 grams of a colorless and stable solid.
-
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83
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0030272259
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T. F. J. Lampe, H. M. R. Hoffmann, U. T. Bornscheuer, Tetrahedron: Asymmetry 1996, 7, 2889-2900.
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See, for example, the enzymatic kinetic resolution of a racemic oxabicyclic dimer resulting from bis-[4+3] cycloaddition with 2,2-methylenedifuran by employing Candida cyclindracea lipase (CCL): a) A. G. Csákÿ, P. Vogel, Tetrahedron: Asymmetry 2000, 11, 4935-4944;
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a) B. J. Bunn, P. J. Cox, N. S. Simpkins, Tetrahedron 1993, 49, 207-218;
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D. Seebach, Angew. Chem. 1988, 100, 1685-1715; Angew. Chem. Int. Ed. Engl. 1988, 27, 1624-1654.
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98
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a) I. Rose, PhD thesis, Universität Hannover 1997;
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Rose, I.1
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H. M. R. Hoffmann, R. Dunkel, M. Mentzel, H. Reuter, C. B. W. Stark, Chem. Eur. J. 2001, 7, 4771-4789.
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102
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4544325443
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note
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Racemic but diastereomerically pure substrates were used in the later stages of the synthesis.
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108
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0006234652
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(Eds.: J. Mulzer, H. Waldmann), Wiley-VCH, Weinheim
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2O solvent mixtures on several organic reactions (for example, Diels-Alder cycloadditions): U. Schmid, H. Waldmann in Organic Synthesis Highlights III (Eds.: J. Mulzer, H. Waldmann), Wiley-VCH, Weinheim, 1998, p. 205.
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37049097003
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J. S. Yadav, C. Srinivas Rao, S. Chandrasekhar, A. V. Rama Rao, Tetrahedron Lett. 1995, 36, 7717-7770; for the synthesis of the racemic C21-C27 segment, see A. V. Rama Rao, J. S. Yadav, V. Vidyasagar, J. Chem. Soc. Chem. Commun. 1985, 55-56.
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111
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T. F. J. Lampe, H. M. R. Hoffmann, Chem. Commun. 1996, 1931-1932; see also: M. Lautens, S. Ma, Tetrahedron Lett. 1996, 37, 1727-1730.
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114
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R. Dunkel, M. Mentzel, H. M. R. Hoffmann, Tetrahedron 1997, 53, 14929-14936.
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Dunkel, R.1
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b) O. Gaertzen, A. M. Misske, P. Wolbers, H. M. R. Hoffmann, Synlett 1999, 1041-1044.
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b) M. Lautens, J.-L. Renaud, S. Hiebert, J. Am. Chem. Soc. 2000, 122, 1804-1805.
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125
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4544246759
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note
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See ref. [74] for the preparation of rac-127.
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126
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0038292195
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Very recently, hodgkinsine and hodgkinsine B, two stereoisomeric members of the polypyrrolidinoindoline alkaloids, were synthesized from a common racemic precursor using a stereoselective, ligand-controlled Heck cyclization: J. J. Kodanko, L. E. Overman, Angew. Chem. 2003, 115, 2632-2635; Angew. Chem. Int. Ed. 2003, 42, 2528-2531.
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0038001590
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Very recently, hodgkinsine and hodgkinsine B, two stereoisomeric members of the polypyrrolidinoindoline alkaloids, were synthesized from a common racemic precursor using a stereoselective, ligand-controlled Heck cyclization: J. J. Kodanko, L. E. Overman, Angew. Chem. 2003, 115, 2632-2635; Angew. Chem. Int. Ed. 2003, 42, 2528-2531.
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128
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4544320772
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L. O. Haustedt, I. V. Hartung, H. M. R. Hoffmann, Angew. Chem. 2003, 115, 2815-2820; Angew. Chem. Int Ed. 2003, 42, 2711-2716.
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84989436180
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H. M. R. Hoffmann, K. Giesel, R. Lies, Z. M. Ismail, Synthesis 1986, 548-550.
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