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Volumn 38, Issue 24, 1997, Pages 4311-4314

Conjugate addition of lithiated Schollkopf's bislactim ether to 1E,3E-Butadienylphosphonates: Stereocontrolled access to 2,3 -anti-4E 2-Amino-6-phosphono-4-hexenoic acid derivatives

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; N METHYL DEXTRO ASPARTIC ACID RECEPTOR BLOCKING AGENT; PHOSPHONOAMINO ACID;

EID: 0030990715     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00888-5     Document Type: Article
Times cited : (18)

References (33)
  • 1
    • 0003772393 scopus 로고
    • Watkins, J.C.; Collingridge, G.L. Eds. Oxford University Press: Oxford
    • a. The NMDA Receptor, 2nd ed.; Watkins, J.C.; Collingridge, G.L. Eds. Oxford University Press: Oxford 1994.
    • (1994) The NMDA Receptor, 2nd Ed.
  • 9
    • 0004218246 scopus 로고
    • Tetrahedron organic chemistry series
    • Baldwin, J. E., Magnus, P.D. Eds.; Pergamon Press: Oxford
    • Permultter, P. Conjugate Addition Reactions in Organic Synthesis, Tetrahedron Organic Chemistry Series; Baldwin, J. E., Magnus, P.D. Eds.; vol. 9, Pergamon Press: Oxford 1992.
    • (1992) Conjugate Addition Reactions in Organic Synthesis , vol.9
    • Permultter, P.1
  • 12
    • 0026528113 scopus 로고
    • and references cited therein
    • c. Minami, T.; Motoyoshiya, J. Synthesis 1992, 333-349, and references cited therein.
    • (1992) Synthesis , pp. 333-349
    • Minami, T.1    Motoyoshiya, J.2
  • 21
    • 0342431919 scopus 로고    scopus 로고
    • note
    • 31P NMR analyses). Spectral data obtained for compounds 6d are in full agreement with those previously reported in ref. 10.
  • 24
    • 37049084556 scopus 로고
    • (3S)-2,5-diethoxy-3-isopropyl-3,6-dihydropyrazine was prepared from glycine and L-valine, by treatment of cyclo[(2S)-valgly] with triethyloxonium tetrafluorborate. See Rose, J.E., Leeson, P.D.; Gani, D. J. Chem. Soc. Perkin Trans. 1 1995, 157-165. Alternatively, both enantiomers of the related 2,5-dimethoxy-3-isopropyl-3,6-dihydropyrazine can be purchased from E. Merck.
    • (1995) J. Chem. Soc. Perkin Trans. 1 , pp. 157-165
    • Rose, J.E.1    Leeson, P.D.2    Gani, D.3
  • 26
    • 0003416750 scopus 로고
    • Organic chemistry series
    • Baldwin, J.E.; Magnus, P.D. Eds.; Pergamon Press: Oxford
    • Absolute configurations follow from the use of 5, derived from L-val, as there is ample precedent: Williams, R.M. Synthesis of Optically Active α-Amino Acids. Organic Chemistry Series; Baldwin, J.E.; Magnus, P.D. Eds.; Pergamon Press: Oxford, 1989; pp 1-34.
    • (1989) Synthesis of Optically Active α-Amino Acids , pp. 1-34
    • Williams, R.M.1
  • 27
    • 0343737030 scopus 로고    scopus 로고
    • note
    • 20 = -14.4 (HC1 1.0M, c = 1.45).
  • 28
    • 0342866408 scopus 로고    scopus 로고
    • note
    • 1H NOE spectroscopy, as depicted in Fig.1.
  • 33
    • 33845278146 scopus 로고
    • Ten-membered trans-fused chair-boat-like transition states have already been drawn to rationalize the stereochemical outcome of the conjugate addition of allyllithium reagents to cyclic enones. See Binns, M.R.; Haynes, R.K.; Katsifis, A.G.; Schober, P.A.; Vonwiller, S.C. J. Am. Chem. Soc. 1988, 110, 5411-5423 and 5423-5433.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 5411-5423
    • Binns, M.R.1    Haynes, R.K.2    Katsifis, A.G.3    Schober, P.A.4    Vonwiller, S.C.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.