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Volumn 68, Issue 11, 2003, Pages 4338-4344

Novel use of N-benzoyl-N, O-acetals as N-acylimine equivalents in asymmetric heterocycloaddition: An extended enantioselective pathway to β-benzamido aldehydes

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOSELECTIVITY;

EID: 0038102458     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0203138     Document Type: Article
Times cited : (47)

References (39)
  • 13
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    • This study exemplified that the nature of the vinyl ether substituent can significantly modulate the stability of the desired heteroadduct.
  • 15
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    • 10a
  • 22
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    • 1H NMR by its vinylic proton at 6.27 ppm (d, J = 14.8 Hz, E geometry).
  • 23
    • 0038432746 scopus 로고    scopus 로고
    • note
    • 1H diastereotopic signals of compounds 2a-c, the chemical shifts of the N,O-acetalic protons H-6 are in the following range: δ endo-β > δ exo-α > δ exo-β.
  • 24
    • 0038093968 scopus 로고    scopus 로고
    • note
    • 3-catalyzed reaction occurred between 3 and the N,O-acetal 5f from which the corresponding N-acylimine 4f could not have been obtained.
  • 25
    • 0037756263 scopus 로고    scopus 로고
    • note
    • A possible rationale would be the poisonous effect of the in situ formed methanol on the lanthanide salt.
  • 26
    • 0033215412 scopus 로고    scopus 로고
    • 2-mediated α-amidoalkylation of ethyl vinyl ether with the use of 6-type N-(1-benzotriazol-1-alkyl)amides: Katritzky, A. R.; Fan, W. Q.; Silina, A. J. Org. Chem. 1999, 64, 7622.
    • (1999) J. Org. Chem. , vol.64 , pp. 7622
    • Katritzky, A.R.1    Fan, W.Q.2    Silina, A.3
  • 27
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    • 4) on the expected stepwise mechanism that would involve this intermediate.
  • 29
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    • 2 and column chromatography gave low yields of purified product (17% for 2e).
  • 30
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    • note
    • 2Me) if we assume that the reaction is disfavored when N,O-acetal is substituted by an electron-withdrawing group.
  • 31
    • 0038770677 scopus 로고    scopus 로고
    • note
    • The -(+)-O-vinyl-pantolactone 3 used in this study was found to have 98.5% ee (determined by chiral GC, see Experimental Section).
  • 33
    • 0001209391 scopus 로고    scopus 로고
    • To our knowledge, 5-type compounds have never been used for the preparation of 2-type 6-alkoxy dihydrooxazines. By contrast, the successful use of N,O-acetals as iminium precursors in the asymmetric preparation of β-aminocarbonyl compounds is well documented, see: (a) Ferraris, D.; Young, B.; Dudding, T.; Leckta, T. J. Am. Chem. Soc. 1998, 120, 4849. (b) Kise, N.; Ueda, N. Org. Lett. 1999, 1, 1803. (c) Kise, N.; Ueda, N. J. Org. Chem. 1999, 64, 7511. (d) Pilli, R. A.; Alves, C. F.; Böckelmann, M. A.; Mascarenhas, Y. P.; Nevy, J. G.; Vencato, I. Tetrahedron Lett. 1999, 40, 2891. (e) Ferraris, D.; Young, B.; Dudding, T.; Leckta, T. J. Am. Chem. Soc. 2002, 124, 67 and references therein.
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    • Ferraris, D.1    Young, B.2    Dudding, T.3    Leckta, T.4
  • 34
    • 0000858505 scopus 로고    scopus 로고
    • To our knowledge, 5-type compounds have never been used for the preparation of 2-type 6-alkoxy dihydrooxazines. By contrast, the successful use of N,O-acetals as iminium precursors in the asymmetric preparation of β-aminocarbonyl compounds is well documented, see: (a) Ferraris, D.; Young, B.; Dudding, T.; Leckta, T. J. Am. Chem. Soc. 1998, 120, 4849. (b) Kise, N.; Ueda, N. Org. Lett. 1999, 1, 1803. (c) Kise, N.; Ueda, N. J. Org. Chem. 1999, 64, 7511. (d) Pilli, R. A.; Alves, C. F.; Böckelmann, M. A.; Mascarenhas, Y. P.; Nevy, J. G.; Vencato, I. Tetrahedron Lett. 1999, 40, 2891. (e) Ferraris, D.; Young, B.; Dudding, T.; Leckta, T. J. Am. Chem. Soc. 2002, 124, 67 and references therein.
    • (1999) Org. Lett. , vol.1 , pp. 1803
    • Kise, N.1    Ueda, N.2
  • 35
    • 0033214855 scopus 로고    scopus 로고
    • To our knowledge, 5-type compounds have never been used for the preparation of 2-type 6-alkoxy dihydrooxazines. By contrast, the successful use of N,O-acetals as iminium precursors in the asymmetric preparation of β-aminocarbonyl compounds is well documented, see: (a) Ferraris, D.; Young, B.; Dudding, T.; Leckta, T. J. Am. Chem. Soc. 1998, 120, 4849. (b) Kise, N.; Ueda, N. Org. Lett. 1999, 1, 1803. (c) Kise, N.; Ueda, N. J. Org. Chem. 1999, 64, 7511. (d) Pilli, R. A.; Alves, C. F.; Böckelmann, M. A.; Mascarenhas, Y. P.; Nevy, J. G.; Vencato, I. Tetrahedron Lett. 1999, 40, 2891. (e) Ferraris, D.; Young, B.; Dudding, T.; Leckta, T. J. Am. Chem. Soc. 2002, 124, 67 and references therein.
    • (1999) J. Org. Chem. , vol.64 , pp. 7511
    • Kise, N.1    Ueda, N.2
  • 36
    • 0033537912 scopus 로고    scopus 로고
    • To our knowledge, 5-type compounds have never been used for the preparation of 2-type 6-alkoxy dihydrooxazines. By contrast, the successful use of N,O-acetals as iminium precursors in the asymmetric preparation of β-aminocarbonyl compounds is well documented, see: (a) Ferraris, D.; Young, B.; Dudding, T.; Leckta, T. J. Am. Chem. Soc. 1998, 120, 4849. (b) Kise, N.; Ueda, N. Org. Lett. 1999, 1, 1803. (c) Kise, N.; Ueda, N. J. Org. Chem. 1999, 64, 7511. (d) Pilli, R. A.; Alves, C. F.; Böckelmann, M. A.; Mascarenhas, Y. P.; Nevy, J. G.; Vencato, I. Tetrahedron Lett. 1999, 40, 2891. (e) Ferraris, D.; Young, B.; Dudding, T.; Leckta, T. J. Am. Chem. Soc. 2002, 124, 67 and references therein.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 2891
    • Pilli, R.A.1    Alves, C.F.2    Böckelmann, M.A.3    Mascarenhas, Y.P.4    Nevy, J.G.5    Vencato, I.6
  • 37
    • 0037045227 scopus 로고    scopus 로고
    • and references therein
    • To our knowledge, 5-type compounds have never been used for the preparation of 2-type 6-alkoxy dihydrooxazines. By contrast, the successful use of N,O-acetals as iminium precursors in the asymmetric preparation of β-aminocarbonyl compounds is well documented, see: (a) Ferraris, D.; Young, B.; Dudding, T.; Leckta, T. J. Am. Chem. Soc. 1998, 120, 4849. (b) Kise, N.; Ueda, N. Org. Lett. 1999, 1, 1803. (c) Kise, N.; Ueda, N. J. Org. Chem. 1999, 64, 7511. (d) Pilli, R. A.; Alves, C. F.; Böckelmann, M. A.; Mascarenhas, Y. P.; Nevy, J. G.; Vencato, I. Tetrahedron Lett. 1999, 40, 2891. (e) Ferraris, D.; Young, B.; Dudding, T.; Leckta, T. J. Am. Chem. Soc. 2002, 124, 67 and references therein.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 67
    • Ferraris, D.1    Young, B.2    Dudding, T.3    Leckta, T.4


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