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Volumn 16, Issue 10, 2005, Pages 1807-1816

Stereoselective addition of organometallic reagents to a chiral acyclic nitrone derived from L-erythrulose

Author keywords

[No Author keywords available]

Indexed keywords

ALUMINUM DERIVATIVE; AMINO ACID DERIVATIVE; DIETHYL ALUMINIUM CHLORIDE; ERYTHRULOSE; LEWIS ACID; NITRONE DERIVATIVE; ORGANOLITHIUM COMPOUND; ORGANOMAGNESIUM; ORGANOMETALLIC COMPOUND; UNCLASSIFIED DRUG; ZINC BROMIDE;

EID: 19344373605     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2005.03.013     Document Type: Article
Times cited : (23)

References (49)
  • 2
    • 0038106171 scopus 로고    scopus 로고
    • R. Bloch Chem. Rev. 98 1998 1407 1438
    • (1998) Chem. Rev. , vol.98 , pp. 1407-1438
    • Bloch, R.1
  • 17
    • 0035952982 scopus 로고    scopus 로고
    • N-Hydroxy amino acids have been found as components of depsipeptide antibiotics: M. Lorca, and M. Kurosu Tetrahedron Lett. 2001 2431 2434
    • (2001) Tetrahedron Lett. , pp. 2431-2434
    • Lorca, M.1    Kurosu, M.2
  • 29
    • 19344376705 scopus 로고    scopus 로고
    • note
    • 9 which was unreactive towards organometallics
  • 31
    • 19344373261 scopus 로고    scopus 로고
    • note
    • We have studied the formation of the nitrone with the aid of quantum-mechanical ab initio methods. The non-isolated E nitrone was found to be more stable than the Z-isomer by over 3 kcal/mol. This indicates that the formation of the Z-nitrone is subject to kinetic control. Preliminary results of studies on possible transition states suggest that that leading to the isolated Z-nitrone is lower in energy than the alternative transition state leading to the E-isomer (unpublished results with S. Safont)
  • 32
    • 19344368164 scopus 로고    scopus 로고
    • note
    • An exception was oxazolidinone 6f, where unequivocal NOE measurements were not possible due to overlapping of the key signals. In this case, however, the configuration was unequivocally determined by means of X-ray diffraction analysis of product 7f
  • 33
    • 19344364634 scopus 로고    scopus 로고
    • note
    • Crystallographic data of 4b, 4e and 7f have been deposited at the Cambridge Crystallographic Data Centre (deposition numbers from CCDC-177985 to CCDC-177987)
  • 44
    • 0035903912 scopus 로고    scopus 로고
    • For an ab initio study of the reaction of Grignard reagents with chiral nitrones, see: P. Merino, and T. Tejero Tetrahedron 57 2001 8125 8128
    • (2001) Tetrahedron , vol.57 , pp. 8125-8128
    • Merino, P.1    Tejero, T.2
  • 47
    • 0003417469 scopus 로고
    • B.M. Trost I. Fleming L.A. Paquette Pergamon Oxford
    • W. Oppolzer B.M. Trost I. Fleming L.A. Paquette Comprehensive Organic Synthesis Vol. 5 1991 Pergamon Oxford Chapter 1.2
    • (1991) Comprehensive Organic Synthesis , vol.5
    • Oppolzer, W.1
  • 49
    • 0030036748 scopus 로고    scopus 로고
    • In EtOAc, another solvent used in this type of reaction: M.-Q. Xie, D.A. Berges, and M.J. Robins J. Org. Chem. 61 1996 5178 5179 decomposition was observed
    • (1996) J. Org. Chem. , vol.61 , pp. 5178-5179
    • Xie, M.-Q.1    Berges, D.A.2    Robins, M.J.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.