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Volumn , Issue 10, 2009, Pages 1619-1624

New concise route to 2-amino-3-hydroxycycloalkanecarboxylic acids by imidate-mediated intramolecular conjugate addition

Author keywords

Amino acids; Heterocycles; Intramolecular conjugate addition; Stereoselectivity

Indexed keywords


EID: 64149128830     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200801173     Document Type: Article
Times cited : (14)

References (46)
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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
    • 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.
  • 8
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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
    • 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
    • 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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    • 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;
    • (1998) Pure Appl. Chem , vol.70 , pp. 285-288
    • Fraser- Reid, B.1    Burgey, C.S.2    Vollerthum, R.3
  • 26
    • 64149094440 scopus 로고    scopus 로고
    • For intramolecular conjugate addition to α,β-unsaturated diphenyl esters, see
    • For intramolecular conjugate addition to α,β-unsaturated diphenyl esters, see:
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    • For an example of intramolecular conjugate addition to α, β-unsaturated sulfones in a carbocyclic system, see
    • For an example of intramolecular conjugate addition to α, β-unsaturated sulfones in a carbocyclic system, see:
  • 32
    • 4143050267 scopus 로고    scopus 로고
    • 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
    • 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,
  • 33
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    • and references therein. For acid-promoted intramolecular epoxide-opening of trichloroacetimidates, see
    • and references therein. For acid-promoted intramolecular epoxide-opening of trichloroacetimidates, see:
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    • and references therein. For the Overman rearrangement, see
    • and references therein. For the Overman rearrangement, see:
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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;
    • 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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    • 1,2-reduction: for la: M.-E. Theoclitou, P. J. Duggan, C. Abell. Bioorg. Med. Chem. Lett. 1996, 6, 1285-1288;
    • 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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    • for lb: L. Fonteneau, S. Rosa, D. Buisson. Tetrahedron: Asymmetry 2002, 13, 579-585.
    • for lb: L. Fonteneau, S. Rosa, D. Buisson. Tetrahedron: Asymmetry 2002, 13, 579-585.
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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.
    • 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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