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Volumn 11, Issue 15, 2009, Pages 3254-3257

The chiral auxiliary N-1-(1′-Naphthyl)ethyl-O-tert- butylhydroxylamine: A chiral weinreb amide equivalent

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; HYDROXYLAMINE; N 1 (1' NAPHTHYL)ETHYL O TERT BUTYLHYDROXYLAMINE; N-1-(1'-NAPHTHYL)ETHYL-O-TERT-BUTYLHYDROXYLAMINE; NAPHTHALENE DERIVATIVE;

EID: 68149147425     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901174t     Document Type: Article
Times cited : (17)

References (56)
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    • For reviews, see
    • For reviews, see: Oppolzer, W. Tetrahedron 1987, 43, 1969.
    • (1987) Tetrahedron , vol.43 , pp. 1969
    • Oppolzer, W.1
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    • For selected recent applications of enantiomerically pure 4-alkyl-5,5-dimethyloxazolidin-2-ones in synthesis from this laboratory, see: a
    • For selected recent applications of enantiomerically pure 4-alkyl-5,5-dimethyloxazolidin-2-ones in synthesis from this laboratory, see: (a) Davies, S. G.; Nicholson, R. L.; Smith, A. D. Synlett 2002, 1637.
    • (2002) Synlett , pp. 1637
    • Davies, S.G.1    Nicholson, R.L.2    Smith, A.D.3
  • 27
    • 68149140571 scopus 로고    scopus 로고
    • Enders, D.; Eichenauer, H. Tetrahedron Lett. 1977, 18, 191. Davenport, K. G.; Eichenauer, H.; Enders, D.; Newcomb, M.; Bergbreiter, D. E. J. Am. Chem. Soc. 1979, 101, 5654.
    • Enders, D.; Eichenauer, H. Tetrahedron Lett. 1977, 18, 191. Davenport, K. G.; Eichenauer, H.; Enders, D.; Newcomb, M.; Bergbreiter, D. E. J. Am. Chem. Soc. 1979, 101, 5654.
  • 28
    • 84985615010 scopus 로고    scopus 로고
    • Enders, D.; Eichenauer, H. Angew. Chem., Int. Ed. Engl. 1979, 18, 397. Enders, D.; Eichenauer, H.; Baus, U.; Schubert, H.; Kremer, K. A. M. Tetrahedron 1984, 40, 1345.
    • Enders, D.; Eichenauer, H. Angew. Chem., Int. Ed. Engl. 1979, 18, 397. Enders, D.; Eichenauer, H.; Baus, U.; Schubert, H.; Kremer, K. A. M. Tetrahedron 1984, 40, 1345.
  • 42
    • 68149135750 scopus 로고    scopus 로고
    • Control of the temperature is critical to the success of this resolution procedure, as an alternative polymorph of the salt, leading to racemic 10, is produced at higher temperatures
    • Control of the temperature is critical to the success of this resolution procedure, as an alternative polymorph of the salt, leading to racemic 10, is produced at higher temperatures.
  • 43
    • 68149120171 scopus 로고    scopus 로고
    • 1H NMR spectroscopic analysis in the presence of (S)-O-acetylmandelic acid as a chiral shift reagent and comparison with an authentic racemic sample.
    • 1H NMR spectroscopic analysis in the presence of (S)-O-acetylmandelic acid as a chiral shift reagent and comparison with an authentic racemic sample.
  • 44
    • 68149105256 scopus 로고    scopus 로고
    • 1H NMR spectrum of the crude reaction mixtures (and the pure products); relatively large chemical shift differences between the tert-butyl singlets of the diastereoisomeric products facilitated this analysis.
    • 1H NMR spectrum of the crude reaction mixtures (and the pure products); relatively large chemical shift differences between the tert-butyl singlets of the diastereoisomeric products facilitated this analysis.
  • 45
    • 68149113465 scopus 로고    scopus 로고
    • Alternatively, the aldehyde and 10 are separable by distillation
    • Alternatively, the aldehyde and 10 are separable by distillation.
  • 47
    • 0010640653 scopus 로고    scopus 로고
    • The enantiomeric excesses of (S)-23 and (R)-24 were determined by reduction and conversion of the resultant alcohol to the corresponding Mosher's ester; see: Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543. Full details are contained within Supporting Information.
    • The enantiomeric excesses of (S)-23 and (R)-24 were determined by reduction and conversion of the resultant alcohol to the corresponding Mosher's ester; see: Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543. Full details are contained within Supporting Information.
  • 50
    • 68149121402 scopus 로고    scopus 로고
    • The enantiomeric excesses of (S)-25, (R)-25, (S)-26, (3S,5R)-27, and (3R,5S)-27 were determined by chiral GC analysis.
    • The enantiomeric excesses of (S)-25, (R)-25, (S)-26, (3S,5R)-27, and (3R,5S)-27 were determined by chiral GC analysis.
  • 54
    • 68149140572 scopus 로고    scopus 로고
    • In these cases, partial oxidation of the auxiliary 10 to the oxime 9 occurred under the reaction conditions. A mixture of 9 and 10 was thus isolated after chromatography, in addition to the desired iodolactones 27 and 28
    • In these cases, partial oxidation of the auxiliary 10 to the oxime 9 occurred under the reaction conditions. A mixture of 9 and 10 was thus isolated after chromatography, in addition to the desired iodolactones 27 and 28.


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