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Volumn , Issue 15, 2000, Pages 2809-2820

Asymmetric synthesis of α-Methyl α-Amino Acids through diastereoselective alkylation under mild reaction conditions of an iminic alanine template with a 1,2,3,6-Tetrahydro-2-Pyrazinone structure

Author keywords

Amino acids; Asymmetric synthesis; Palladium; Phase transfer catalysis; Pyrazinones

Indexed keywords

1,2,3,6 TETRAHYDRO 2 PYRAZINONE; ALANINE; ALPHA AMINO ACID; IMINE; PALLADIUM; PYRAZINOIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0037844251     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200008)2000:15<2809::AID-EJOC2809>3.0.CO;2-X     Document Type: Article
Times cited : (29)

References (69)
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    • note
    • Naturally occurring antibiotics such as lactacistin, conagenin, altemicidin, myomicin and sphingofungins are structurally complex AMAAs.
  • 28
    • 0032572894 scopus 로고    scopus 로고
    • [8e] S. Kobayashi, M. Matsumara, T. Furuta, T. Hayashi, S. Iwamoto, Synlett 1997, 301-303; S. Kobayashi, T. Furuta, Tetrahedron 1998, 54, 10275-10294.
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  • 54
    • 0005324689 scopus 로고
    • To our knowledge, the only reported example of these kinds of heterocycles is the case of 1,2,3,6-tetrahydro-6,6-dimethyl-5-phenyl-2-pyrazinone, prepared by the reaction of 2,2-dimethyl-3-phenyl-2H-azirine with glycine ethyl ester: G. Alvernhe, A. Laurent, A. Masroua, Tetrahedron Lett. 1983, 24, 1153-1156.
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    • Alvernhe, G.1    Laurent, A.2    Masroua, A.3
  • 55
    • 0029025244 scopus 로고
    • The chiral amino ketone was recently prepared from N-Cbz-(S)-valine N-methoxy-N-methyl amide, but no experimental yield and analytical data were reported: P. Edwards, D. J. Wolanin, D. W. Andisik, M. W Davis, J. Med. Chem. 1995, 38, 76-85.
    • (1995) J. Med. Chem. , vol.38 , pp. 76-85
    • Edwards, P.1    Wolanin, D.J.2    Andisik, D.W.3    Davis, M.W.4
  • 56
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    • and references cited therein
    • The racemic compound was also reported: A. Guzmán, C. Quintero, J. M. Muchowski. Can. J. Chem. 1991, 69, 2059-2063, and references cited therein.
    • (1991) Can. J. Chem. , vol.69 , pp. 2059-2063
    • Guzmán, A.1    Quintero, C.2    Muchowski, J.M.3
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    • 0342989216 scopus 로고    scopus 로고
    • Hyperchem from Hypercube was used for these calculations
    • Hyperchem from Hypercube was used for these calculations.
  • 60
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    • Y. N. Belokon', N. I. Chernoglazova, A. S. Batsanov, N. S. Garbalinskaya, V. I. Bakhmutov, Y. T. Struchkov, V. M. Belikov, Izv. Akad Nauk SSSR, Ser.Khim. 1987, 4, 852-857; Chem. Abstr. 1988, 108, 801, 132255v.
    • (1988) Chem. Abstr. , vol.108 , pp. 801
  • 64
    • 0031585053 scopus 로고    scopus 로고
    • The palladium(0)-catalyzed addition of benzophenone imine of α-aminoacetonitrile to vinyloxiranes has been previously described: A. Mazón, C. Nájera, J. Ezquerra, C. Pedregal, Tetrahedron Lett. 1997, 38, 2167-2170.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 2167-2170
    • Mazón, A.1    Nájera, C.2    Ezquerra, J.3    Pedregal, C.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.