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Volumn 76, Issue 9, 2011, Pages 3139-3150

Cyclic sulfur ylides derived from gleason-type chiral auxiliaries for the asymmetric synthesis of epoxy amides

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC SYNTHESIS; BASIC CONDITIONS; CHIRAL AUXILIARIES; ENANTIOMERIC EXCESS; EPOXY ALCOHOLS; L-AMINO ACIDS; L-SERINE; L-VALINE; SULFONIUM SALTS; SULFUR YLIDES;

EID: 79955549980     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo1025964     Document Type: Article
Times cited : (25)

References (64)
  • 30
    • 79955564192 scopus 로고    scopus 로고
    • note
    • See Supporting Information for details of the analyses by HPLC and GC-MS for the determination of the ee's.
  • 31
    • 79955563486 scopus 로고    scopus 로고
    • note
    • 1H NMR spectra the presence of a mixture of cis: trans epoxyalcohols whose proportions were determined directly from the crude reactions.
  • 32
    • 0029064047 scopus 로고
    • cis epoxy alcohols 3′f, 3′g, 3′h, and 3′i have been described in the following articles, respectively
    • cis epoxy alcohols 3′f, 3′g, 3′h, and 3′i have been described in the following articles, respectively: Soulié, J.; Péricaud, F.; Lallemand, J. Y. Tetrahedron: Asymmetry 1995, 6, 1367-1374
    • (1995) Tetrahedron: Asymmetry , vol.6 , pp. 1367-1374
    • Soulié, J.1    Péricaud, F.2    Lallemand, J.Y.3
  • 43
    • 79955567991 scopus 로고    scopus 로고
    • note
    • Molecular modelling studies were performed by DFT calculations with Gaussian 03, using a B3LYP/6-31+G(d) as the force field for a system in solution by means of a PCM (polarizable continuum model), choosing ethanol as solvent.
  • 44
    • 0037157083 scopus 로고    scopus 로고
    • This eclipsed orientation of both polar groups is supported by rigorous and extensive theoretical studies of this reaction undertaken by Aggarwal et al.
    • This eclipsed orientation of both polar groups is supported by rigorous and extensive theoretical studies of this reaction undertaken by Aggarwal et al.: Aggarwal, V. K.; Jeremy, J. N.; Richardson, J. J. Am. Chem. Soc. 2002, 124, 5747-5756
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 5747-5756
    • Aggarwal, V.K.1    Jeremy, J.N.2    Richardson, J.3
  • 47
    • 79955562665 scopus 로고    scopus 로고
    • note
    • This amino acid derivative is commercially available.
  • 49
    • 0000830825 scopus 로고
    • For synthetic applications of 2,3-epoxy alcohols, see
    • For synthetic applications of 2,3-epoxy alcohols, see: Hanson, R. M. Chem. Rev. 1991, 91, 437-475
    • (1991) Chem. Rev. , vol.91 , pp. 437-475
    • Hanson, R.M.1
  • 54
    • 79955570432 scopus 로고    scopus 로고
    • note
    • Cyclic amide 5 is commercially available and was described by Gleason, J. L.; see ref 11.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.