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For a recent account on the face-to-face and center-to-edge interactions on aromatic systems and polar effects, see: a) F. Cozzi, R. Annunziata, M. Benaglia, M. Cinquini, L. Raimondi, K. K. Baldridge, J. S. Siegel, Org. Biomol. Chem. 2003, 1, 157; b) For a recent review on the arene-arene, π stacking, and C-H/ π interactions, see: E. A. Meyer, R. K. Castellano, F. Diederich, Angew. Chem. 2003, 115, 1244; Angew. Chem. Int. Ed. 2003, 42, 1210; c) For C-H/π interactions, see: P. Hobza, Z. Havlas, Chem. Rev. 2000, 100, 4253; d) For a review on π shielding in organic synthesis, see: G. B. Jones, Tetrahedron 2001, 57, 7999.
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For a recent account on the face-to-face and center-to-edge interactions on aromatic systems and polar effects, see: a) F. Cozzi, R. Annunziata, M. Benaglia, M. Cinquini, L. Raimondi, K. K. Baldridge, J. S. Siegel, Org. Biomol. Chem. 2003, 1, 157; b) For a recent review on the arene-arene, π stacking, and C-H/ π interactions, see: E. A. Meyer, R. K. Castellano, F. Diederich, Angew. Chem. 2003, 115, 1244; Angew. Chem. Int. Ed. 2003, 42, 1210; c) For C-H/π interactions, see: P. Hobza, Z. Havlas, Chem. Rev. 2000, 100, 4253; d) For a review on π shielding in organic synthesis, see: G. B. Jones, Tetrahedron 2001, 57, 7999.
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For a recent account on the face-to-face and center-to-edge interactions on aromatic systems and polar effects, see: a) F. Cozzi, R. Annunziata, M. Benaglia, M. Cinquini, L. Raimondi, K. K. Baldridge, J. S. Siegel, Org. Biomol. Chem. 2003, 1, 157; b) For a recent review on the arene-arene, π stacking, and C-H/ π interactions, see: E. A. Meyer, R. K. Castellano, F. Diederich, Angew. Chem. 2003, 115, 1244; Angew. Chem. Int. Ed. 2003, 42, 1210; c) For C-H/π interactions, see: P. Hobza, Z. Havlas, Chem. Rev. 2000, 100, 4253; d) For a review on π shielding in organic synthesis, see: G. B. Jones, Tetrahedron 2001, 57, 7999.
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For a recent account on the face-to-face and center-to-edge interactions on aromatic systems and polar effects, see: a) F. Cozzi, R. Annunziata, M. Benaglia, M. Cinquini, L. Raimondi, K. K. Baldridge, J. S. Siegel, Org. Biomol. Chem. 2003, 1, 157; b) For a recent review on the arene-arene, π stacking, and C-H/ π interactions, see: E. A. Meyer, R. K. Castellano, F. Diederich, Angew. Chem. 2003, 115, 1244; Angew. Chem. Int. Ed. 2003, 42, 1210; c) For C-H/π interactions, see: P. Hobza, Z. Havlas, Chem. Rev. 2000, 100, 4253; d) For a review on π shielding in organic synthesis, see: G. B. Jones, Tetrahedron 2001, 57, 7999.
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For a recent account on the face-to-face and center-to-edge interactions on aromatic systems and polar effects, see: a) F. Cozzi, R. Annunziata, M. Benaglia, M. Cinquini, L. Raimondi, K. K. Baldridge, J. S. Siegel, Org. Biomol. Chem. 2003, 1, 157; b) For a recent review on the arene-arene, π stacking, and C-H/ π interactions, see: E. A. Meyer, R. K. Castellano, F. Diederich, Angew. Chem. 2003, 115, 1244; Angew. Chem. Int. Ed. 2003, 42, 1210; c) For C-H/π interactions, see: P. Hobza, Z. Havlas, Chem. Rev. 2000, 100, 4253; d) For a review on π shielding in organic synthesis, see: G. B. Jones, Tetrahedron 2001, 57, 7999.
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Jones, G.B.1
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0042027014
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note
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The π stacking has also been proposed by Hayashi to account for the high catalytic activity of a chiral 2,2′-bipyridine-N,N-bisoxide.[4]
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0027408256
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b) N. W. Alcock, J. M. Brown, D. I. Hulmes, Tetrahedron: Asymmetry 1993, 4, 743.
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Š. Vyskočil, L. Meca, I. Tišlerová, I. Císařová, M. Polášek, S. R. Harutyunyan, Y. N. Belokon, R. M. J. Stead, L. Farrugia, S. C. Lockhart, W. L. Mitchell, P. Kočovský, Chem. Eur. J. 2002, 8, 4633.
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30
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0042527849
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note
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For the previous use of binol to resolve bipyridine-type N,N-bisoxides, see refs [3,4].
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31
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0042027016
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note
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While this work was in progress, Nakajima published the same synthesis of (+)-11, including the resolution with -(-)-binol.[3d] However, this synthesis was mentioned as a footnote without specifying the conditions and the absolute configuration of (+)-11 was not determined.
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32
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0042027015
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note
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F(obs) = 0.0395.
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33
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0042527848
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note
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Investigation of the allylation of 1a with 2, catalyzed by -(+)-11 of 29%, 50%, and 75% ee, respectively, has demonstrated a fully linear relationship between the enantiopurity of the catalyst and the product. In these experiments, the resulting product 3a was of 27%, 45%, and 71% ee, respectively.
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34
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0032522196
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Chloroform has been shown to be the solvent that most strongly stabilizes the arene-arene interactions: G. A. Breault, C. A. Hunter, P. C. Mayers, J. Am. Chem. Soc. 1998, 120, 3402.
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39
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0000009579
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For a discussion on cyclic/open transition state, see: a) S. E. Denmark, N. G. Almstead, J. Org. Chem. 1994, 59, 5130; b) S. E. Denmark, S. Hosoi, J. Org. Chem. 1994, 59, 5133.
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0000032965
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For a discussion on cyclic/open transition state, see: a) S. E. Denmark, N. G. Almstead, J. Org. Chem. 1994, 59, 5130; b) S. E. Denmark, S. Hosoi, J. Org. Chem. 1994, 59, 5133.
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Denmark, S.E.1
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41
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0042527847
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note
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Hayashi has proposed π-π stacking of 1 and the catalysts but, in his case, the variation of the enantioselectivity was less dramatic (94% ee for 1d and 56% ee for 1l as the extremes of the scale).[4] Furthermore, his catalyst gave the best results in MeCN, which is known not to support arene-arene interactions,[15] thus suggesting that his and our catalyst may operate through a different mode of interactions.
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