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Volumn 15, Issue 20, 2009, Pages 5090-5095

Highly selective stereodivergent synthesis of separable amide rotamers, by using Pd chemistry, and their thermodynamic behavior

Author keywords

Allylation; Amides; Palladium; Rotamers stereodivergence

Indexed keywords

ALLYLATION; ANILIDES; CLAISEN REARRANGEMENT; EQUILIBRIUM MIXTURES; PD CATALYST; ROTAMER; ROTAMERS; ROTAMERS STEREODIVERGENCE; STEREODIVERGENT SYNTHESIS; THERMODYNAMIC BEHAVIORS;

EID: 66149110754     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200802627     Document Type: Article
Times cited : (17)

References (42)
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    • For examples of separable amide rotamers, see: a A. Mannschreck, Tetrahedron Lett. 1965, 6, 1341-1347;
    • For examples of separable amide rotamers, see: a) A. Mannschreck, Tetrahedron Lett. 1965, 6, 1341-1347;
  • 15
    • 0031438042 scopus 로고    scopus 로고
    • For papers on conformational analysis of o-tert-butylanilide derivatives by other groups, see: a D. P. Curran, G. R. Hale, S. J. Geib, A. Balog, Q. B. Cass, A. L. G. Degani, M. Z. Hemandes, L. C. G Freitas, Tetrahedron: Asymmetry 1997, 8, 3955-3975;
    • For papers on conformational analysis of o-tert-butylanilide derivatives by other groups, see: a) D. P. Curran, G. R. Hale, S. J. Geib, A. Balog, Q. B. Cass, A. L. G. Degani, M. Z. Hemandes, L. C. G Freitas, Tetrahedron: Asymmetry 1997, 8, 3955-3975;
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    • A. D. Hughes, D. A. Price, N. S. Simpkins, J. Chem. Soc. Perkin Trans. 1 1999, 1295-1304;
    • b) A. D. Hughes, D. A. Price, N. S. Simpkins, J. Chem. Soc. Perkin Trans. 1 1999, 1295-1304;
  • 20
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    • For a preliminary communication of this work, see
    • For a preliminary communication of this work, see: N. Ototake, T. Taguchi, O. Kitagawa, Tetrahedron Lett. 2008, 49, 5458-5460.
    • (2008) Tetrahedron Lett , vol.49 , pp. 5458-5460
    • Ototake, N.1    Taguchi, T.2    Kitagawa, O.3
  • 23
    • 0037131449 scopus 로고    scopus 로고
    • It is well known that in secondary amides, Z rotamers are thermody-namically more stable than E rotamers
    • Angew. Chem. Int. Ed. 2002, 41, 3854-3857. It is well known that in secondary amides, Z rotamers are thermody-namically more stable than E rotamers.
    • (2002) Angew. Chem. Int. Ed , vol.41 , pp. 3854-3857
  • 24
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    • J. Tsuji, J. Synth. Org. Chem. Jpn. 1999, 57, 1036-1050;
    • a) J. Tsuji, J. Synth. Org. Chem. Jpn. 1999, 57, 1036-1050;
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    • The allylation of o-tert-butylanilide using a π-allyl-Pd catalyst directly gave an N-allylated product without the formation of an O-allylation product. a O. Kitagawa, M. Kohriyama, T. Taguchi, J. Org. Chem. 2002, 67, 8682-8684;
    • The allylation of o-tert-butylanilide using a π-allyl-Pd catalyst directly gave an N-allylated product without the formation of an O-allylation product. a) O. Kitagawa, M. Kohriyama, T. Taguchi, J. Org. Chem. 2002, 67, 8682-8684;
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    • For typical examples, see: a
    • For typical examples, see: a) L. E. Overman, Acc. Chem. Res. 1980, 13, 218-224;
    • (1980) Acc. Chem. Res , vol.13 , pp. 218-224
    • Overman, L.E.1
  • 36
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    • N-Allylanilides 2a-2h in toluene were heated until the changes of E/Z ratios became negligible (reaction time described in Table 5). On the other hand, although thermal isomerization of franyl derivative 2i (E rotamer) was also investigated, the exact equilibrium ratio ((E)-2i/ (Z)-2i) could not be determined, because of the intramolecular Diels-Alder products generated from (Z)-2i.
    • N-Allylanilides 2a-2h in toluene were heated until the changes of E/Z ratios became negligible (reaction time described in Table 5). On the other hand, although thermal isomerization of franyl derivative 2i (E rotamer) was also investigated, the exact equilibrium ratio ((E)-2i/ (Z)-2i) could not be determined, because of the intramolecular Diels-Alder products generated from (Z)-2i.
  • 37
    • 66149157067 scopus 로고    scopus 로고
    • For typical papers on the E-rotamer preference of N-alkylated anilide derivatives, see: a B. F. Pederson, B. Pederson, Tetrahedron 1956, 2995-3001;
    • For typical papers on the E-rotamer preference of N-alkylated anilide derivatives, see: a) B. F. Pederson, B. Pederson, Tetrahedron 1956, 2995-3001;
  • 40
    • 33751156319 scopus 로고    scopus 로고
    • The E-rotamer preference of N-methylanilides has been rationalized on the basis of such an n-π interaction: S. Saito, Y. Toriumi, N. Tomioka, A. Itai, J. Org. Chem. 1995, 60, 4715-4720.
    • The E-rotamer preference of N-methylanilides has been rationalized on the basis of such an n-π interaction: S. Saito, Y. Toriumi, N. Tomioka, A. Itai, J. Org. Chem. 1995, 60, 4715-4720.
  • 41
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    • All calculations were carried out by using the GAMESS (US) package: M. W. Schmidt, K. K. Baldridge, J. A. Boatz, S. T. Elbert, M. S. Gordon, J. H. Jensen, S. Koseki, N. Matsunaga, K. A. Nguyen, S. Su, T. L. Windus, M. Dupuis, J. A. Montgomery, J. Comput. Chem. 1993, 14, 1347-1363.
    • All calculations were carried out by using the GAMESS (US) package: M. W. Schmidt, K. K. Baldridge, J. A. Boatz, S. T. Elbert, M. S. Gordon, J. H. Jensen, S. Koseki, N. Matsunaga, K. A. Nguyen, S. Su, T. L. Windus, M. Dupuis, J. A. Montgomery, J. Comput. Chem. 1993, 14, 1347-1363.
  • 42
    • 66149113411 scopus 로고    scopus 로고
    • CCDC 713422 ((E)-2d) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam. ac.uk/data-request/cif.
    • CCDC 713422 ((E)-2d) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam. ac.uk/data-request/cif.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.