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For the most recent paper on helical secondary structures of α/β-peptides containing β-residues derived from ACPC, see: S. H. Choi, I. A. Guzei, L. C. Spencer, S. II. Gellman, J. Am. Chem. Soc. 2008, 130, 6544-6550
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For the most recent paper on helical secondary structures of α/β-peptides containing β-residues derived from ACPC, see: S. H. Choi, I. A. Guzei, L. C. Spencer, S. II. Gellman, J. Am. Chem. Soc. 2008, 130, 6544-6550.
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12-Helical β-peptides that incorporate 3-methoxy- or 3-phenoxy-substituted ACPC residues have also been reported, see: M. G. Woll, J. D. Fish, P. R. LePlae, S. II. Gellman, J. Am. Chem. Soc. 2002, 124, 12447-12452
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12-Helical β-peptides that incorporate 3-methoxy- or 3-phenoxy-substituted ACPC residues have also been reported, see: M. G. Woll, J. D. Fish, P. R. LePlae, S. II. Gellman, J. Am. Chem. Soc. 2002, 124, 12447-12452.
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For the most recent paper on helical secondary structures of β-peptides containing residues derived from ACHC, see: M. Lee, T. L. Raguse, M. Schinneri, W. C. Pomerantz, X. Wang, P. Wipf, S. H. Gellman, Org. Lett. 2007, 9, 1801-1804
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For the most recent paper on helical secondary structures of β-peptides containing residues derived from ACHC, see: M. Lee, T. L. Raguse, M. Schinneri, W. C. Pomerantz, X. Wang, P. Wipf, S. H. Gellman, Org. Lett. 2007, 9, 1801-1804.
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24
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0000826171
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Intramolecular conjugate addition reactions of trichloroacetimidates to an α,β-unsaturated ester in a carbocyclic system has never been reported. Two examples of such an addition in a heterocyclic system have been reported. For intramolecular conjugate addition to α, β-unsaturated nitriles, see: a
-
Intramolecular conjugate addition reactions of trichloroacetimidates to an α,β-unsaturated ester in a carbocyclic system has never been reported. Two examples of such an addition in a heterocyclic system have been reported. For intramolecular conjugate addition to α, β-unsaturated nitriles, see: a) B. Fraser- Reid, C. S. Burgey, R. Vollerthum, Pure Appl. Chem. 1998, 70, 285-288;
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b) R. Alonso, C. S. Burgey, B. V. Rao, G. D. Vite, R. Vollerthum, M. A. Zottola, B. Fraser-Reid, J. Am. Chem. Soc. 1993, 115, 6666-6672.
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26
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64149094440
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For intramolecular conjugate addition to α,β-unsaturated diphenyl esters, see
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For intramolecular conjugate addition to α,β-unsaturated diphenyl esters, see:
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30
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64149119533
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For an example of intramolecular conjugate addition to α, β-unsaturated sulfones in a carbocyclic system, see
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For an example of intramolecular conjugate addition to α, β-unsaturated sulfones in a carbocyclic system, see:
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32
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4143050267
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Some useful reactions involving trichloroacetimidates for the introduction of nitrogen functionalities have been reported. For electrophile-promoted intramolecular animations of trichloroacetimidates derived from allylic and homoallylic alcohols, see: a H.-S. Lee, S. H. Kang, Synlett 2004, 1673-1685
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Some useful reactions involving trichloroacetimidates for the introduction of nitrogen functionalities have been reported. For electrophile-promoted intramolecular animations of trichloroacetimidates derived from allylic and homoallylic alcohols, see: a) H.-S. Lee, S. H. Kang, Synlett 2004, 1673-1685,
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33
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64149110314
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and references therein. For acid-promoted intramolecular epoxide-opening of trichloroacetimidates, see
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and references therein. For acid-promoted intramolecular epoxide-opening of trichloroacetimidates, see:
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35
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84987190612
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c) U. Schmidt, M. Responded A. Lieberknecht, J. Werner, O. Fischer, Synthesis 1989, 256-261;
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e) Y. Matsushinia, T. Nakayama, S. Tohyama, T. Eguchi, K. Kakinuma, J. Chem. Soc. Perkin Trans. 1 2001, 569-577;
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f) C. Rondot. P. Retailleau, J. Zhu, Org. Lett. 2007, 9, 247-250,
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39
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64149100733
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and references therein. For the Overman rearrangement, see
-
and references therein. For the Overman rearrangement, see:
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42
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6444238708
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The known starting allylic alcohols la and lb were respectively prepared from the corresponding methyl cycloalk-1-enecarboxylales according to the following literature methods. Allylic oxidation: A. J. Catino, R. E. Forslund, M. P. Doyle, J. Am. Chem. Soc. 2004, 126, 13622-13623;
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The known starting allylic alcohols la and lb were respectively prepared from the corresponding methyl cycloalk-1-enecarboxylales according to the following literature methods. Allylic oxidation: A. J. Catino, R. E. Forslund, M. P. Doyle, J. Am. Chem. Soc. 2004, 126, 13622-13623;
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43
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0029920060
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1,2-reduction: for la: M.-E. Theoclitou, P. J. Duggan, C. Abell. Bioorg. Med. Chem. Lett. 1996, 6, 1285-1288;
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1,2-reduction: for la: M.-E. Theoclitou, P. J. Duggan, C. Abell. Bioorg. Med. Chem. Lett. 1996, 6, 1285-1288;
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44
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0037134293
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for lb: L. Fonteneau, S. Rosa, D. Buisson. Tetrahedron: Asymmetry 2002, 13, 579-585.
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for lb: L. Fonteneau, S. Rosa, D. Buisson. Tetrahedron: Asymmetry 2002, 13, 579-585.
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46
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64149105100
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The irradiation of 1-H of compound 6a yielded an NOE of around 8 % on 2-H and around 1 % on 3-H, whereas a small NOE (ca. 1 %) was observed on the NH proton. In contrast, irradiation of the hydrogen corresponding to compound 5a yielded an NOE of around 4% on the NH proton, whereas no NOE was observed on 2-H and 3-H. Irradiation of 1-H of compound 6b yielded an NOE of around 8 % on 2-H and 3- H, whereas almost no NOE was observed on the NH proton. In contrast, irradiation of the hydrogen corresponding to compound 5b yielded an NOE of around 4 % on the NH proton, whereas no NOE was observed on 2-H and 3-H.
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The irradiation of 1-H of compound 6a yielded an NOE of around 8 % on 2-H and around 1 % on 3-H, whereas a small NOE (ca. 1 %) was observed on the NH proton. In contrast, irradiation of the hydrogen corresponding to compound 5a yielded an NOE of around 4% on the NH proton, whereas no NOE was observed on 2-H and 3-H. Irradiation of 1-H of compound 6b yielded an NOE of around 8 % on 2-H and 3- H, whereas almost no NOE was observed on the NH proton. In contrast, irradiation of the hydrogen corresponding to compound 5b yielded an NOE of around 4 % on the NH proton, whereas no NOE was observed on 2-H and 3-H.
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