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Volumn 8, Issue 14, 1997, Pages 2381-2401

Stereoselective Grignard reactions to α-amino nitrones. Synthesis of optically active α-aminohydroxylamines and 1,2-diamines

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXYLAMINE; MAGNESIUM DERIVATIVE; REAGENT;

EID: 0030761511     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00250-4     Document Type: Article
Times cited : (51)

References (107)
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    • (a) Volkmann, R.A. Nucleophilic Addition to Imine and Imine Derivatives In Comprehensive Organic Synthesis., Trost, B.M.; Fleming, I. (Eds.), Pergamon Press, Oxford, 1991, Vol. 1, pp. 355-396.
    • (1991) Comprehensive Organic Synthesis , vol.1 , pp. 355-396
    • Volkmann, R.A.1
  • 2
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    • Formation of C-C bonds by addition to imino groups
    • Houben-Weyl. Helmchen, G.; Hoffmann, R.W.; Mulzer, J.; Schaumann, E. (Eds.) Georg Thieme Verlag, Stuttgart
    • (b) Risen, N.; Arend, M. Formation of C-C Bonds by Addition to Imino Groups In Stereoselective Synthesis, Houben-Weyl. Helmchen, G.; Hoffmann, R.W.; Mulzer, J.; Schaumann, E. (Eds.) Georg Thieme Verlag, 1996, Stuttgart, Vol.3, pp. 1833-1930,
    • (1996) Stereoselective Synthesis , vol.3 , pp. 1833-1930
    • Risen, N.1    Arend, M.2
  • 46
    • 0343004024 scopus 로고    scopus 로고
    • note
    • -)R).
  • 47
    • 0027369640 scopus 로고
    • The 1,2-diamino unit attracts considerable increasing interest since it has been shown to play key roles in medicinal chemistry and asymmetric synthesis. For leading references see: (a) Nakajima, M.; Tomioka, K.; Koga, K. Tetrahedron 1993, 49, 9751-9758.
    • (1993) Tetrahedron , vol.49 , pp. 9751-9758
    • Nakajima, M.1    Tomioka, K.2    Koga, K.3
  • 80
    • 0343875369 scopus 로고
    • Rzepa, H.S.; Goodman, J.G. (Eds.), CD-ROM, Royal Society of Chemistry Publications
    • We have recently described that the α-amino protective groups of L-serine derived nitrones are crucial for the stereoselective course of nucleophilic additions (see ref. 13). See also: Lanaspa, A.; Merchan, F.L.; Merino, P.; Tejero, T.; Dondoni, A. Electronic Conference on Trends in Organic Chemistry (ECTOC-1). Rzepa, H.S.; Goodman, J.G. (Eds.), CD-ROM, Royal Society of Chemistry Publications, 1995.
    • (1995) Electronic Conference on Trends in Organic Chemistry (ECTOC-1)
    • Lanaspa, A.1    Merchan, F.L.2    Merino, P.3    Tejero, T.4    Dondoni, A.5
  • 86
  • 95
    • 0343875367 scopus 로고
    • (JCPE PO81), Stewart, J.J.P. Stewart Computational Chemistry, Colorado Springs, CO, USA and Fujitsu, Ltd., Tokyo, Japan
    • MOPAC 93 Rev. 2 (JCPE PO81), Stewart, J.J.P. Stewart Computational Chemistry, Colorado Springs, CO, USA and Fujitsu, Ltd., Tokyo, Japan, 1993.
    • (1993) MOPAC 93 Rev. , vol.2
  • 97
    • 0343875368 scopus 로고    scopus 로고
    • note
    • In order to simplify calculations, the tert-butoxy group was replaced by a methoxy group and the benzyl group of the nitrone moiety was replaced by a methyl group. Dihedral angles were increased in 10 degrees increments. Also, both dihedral angles β and γ were considered in addition to α in order to ensure that the stationery points given as minima correspond to absolute minima of energy. In fact, for nitrones 5 and 6, three and two conformers very proximal in energy (less than 1 Kcal/mol) were obtained, respectively. Nevertheless, all of them correspond to a model like that depicted in Figure 5 since the only difference stemmed in the values of γ, the rest of parameters being almost identical.
  • 98
    • 0343875366 scopus 로고    scopus 로고
    • note
    • 1H NMR spectra of nitrones 4-6 showed the corresponding signals of the NH groups at higher chemical shifts than other NHBoc derivatives (see experimental).
  • 101
    • 0343004013 scopus 로고    scopus 로고
    • Ventura, O.N.; Cachau, R.E. (Eds.). Montevideo Theoretical Chemistry Laboratory. Universidad de la Republica. Montevideo (Uruguay). See also ref. 6
    • Merchan, F.L.; Merino, P.; Tejero, T. The Molecular Modelling Electronic Conference. (TMMeC-1). Ventura, O.N.; Cachau, R.E. (Eds.). Montevideo Theoretical Chemistry Laboratory. Universidad de la Republica. Montevideo (Uruguay). 1997. Internet: http://uqbar.ncifcrf.gov/agora/. See also ref. 6.
    • (1997) The Molecular Modelling Electronic Conference. (TMMeC-1)
    • Merchan, F.L.1    Merino, P.2    Tejero, T.3
  • 105
    • 0343875364 scopus 로고    scopus 로고
    • note
    • 3) δ 18.99, 20.87, 28.00, 29.64, 53.79, 59.02, 78.65, 125.80, 128.57, 128.81, 136.18, 156.14.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.