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Volumn 46, Issue 7, 1998, Pages 1094-1101

Synthesis of optically active (2-arylvinyl)glycine derivatives by palladium-catalyzed arylation of (s)-n-(benzyloxycarbonyl)vinylglycine

Author keywords

(2 arylvinyl)glycine chiral synthesis; Chiral HPLC; Enantiomeric excess; Palladium catalyzed coupling; Stereoselectivity; Vinylglycine arylation

Indexed keywords

2 [(BENZYLOXYCARBONYL)AMINO] 4 (1 NAPHTHYL) 3 BUTENOIC ACID; 2 [(BENZYLOXYCARBONYL)AMINO] 4 (2 METHOXYPHENYL) 3 BUTENOIC ACID; 2 [(BENZYLOXYCARBONYL)AMINO] 4 (2 METHYLPHENYL) 3 BUTENOIC ACID; 2 [(BENZYLOXYCARBONYL)AMINO] 4 (3 METHYLPHENYL) 3 BUTENOIC ACID; 2 [(BENZYLOXYCARBONYL)AMINO] 4 (4 METHOXYPHENYL) 3 BUTENOIC ACID; 2 [(BENZYLOXYCARBONYL)AMINO] 4 (4 METHYLPHENYL) 3 BUTENOIC ACID; 2 [(BENZYLOXYCARBONYL)AMINO] 4 PHENYL 3 BUTENOIC ACID; BICARBONATE; GLYCINE DERIVATIVE; HETEROCYCLIC COMPOUND; IODINE DERIVATIVE; N (BENZYLOXYCARBONYL)VINYLGLYCINE; PALLADIUM; UNCLASSIFIED DRUG;

EID: 0031827671     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.46.1094     Document Type: Article
Times cited : (6)

References (33)
  • 4
    • 0007663928 scopus 로고
    • For enzymatic resolution of styrylglycine derivatives, see a) Sakota N., Okita K., Matsui Y., Bull. Chem. Soc. Jpn., 43, 1138-1141 (1970); b) Morgan J., Pinhey J. T., Sherry C. J., J. Chem. Soc., Perkin Trans. 1, 1997, 613-619.
    • (1970) Bull. Chem. Soc. Jpn. , vol.43 , pp. 1138-1141
    • Sakota, N.1    Okita, K.2    Matsui, Y.3
  • 5
    • 33748736445 scopus 로고    scopus 로고
    • For enzymatic resolution of styrylglycine derivatives, see a) Sakota N., Okita K., Matsui Y., Bull. Chem. Soc. Jpn., 43, 1138-1141 (1970); b) Morgan J., Pinhey J. T., Sherry C. J., J. Chem. Soc., Perkin Trans. 1, 1997, 613-619.
    • J. Chem. Soc., Perkin Trans. 1 , vol.1997 , pp. 613-619
    • Morgan, J.1    Pinhey, J.T.2    Sherry, C.J.3
  • 16
    • 3543033137 scopus 로고    scopus 로고
    • Earlier references cited in refs. 4 and 11a
    • b) Earlier references cited in refs. 4 and 11a;
  • 29
    • 3543026600 scopus 로고    scopus 로고
    • n) Blaskovich M. A., Wong A. W., Lajoie G. A., Pept. 1994, Proc. Eur. Pept. Symp., 23rd 1994 (Pub. 1995), 205-206 [Chem. Abstr., 126, 8565d (1997)].
    • (1997) Chem. Abstr. , vol.126
  • 30
    • 3543029537 scopus 로고    scopus 로고
    • note
    • Compound 2, which was contaminated with a small amount of the deiodo compound, was recovered in 74% yield after the reaction at 45 °C for 388 h; 12 (74%) was recovered together with the deiodo compound (7%) after 128 h; 13 underwent hydrolysis at the sugar moiety to provide a complex mixture of products after 24 h.
  • 31
    • 0001153586 scopus 로고
    • The product was identical (by comparison of the IR spectrum and TLC mobility) with a commercial sample (purchased from Tokyo Chemical Industry Co., Ltd.). The formation of this compound has been reported in the palladium-catalyzed reaction between 7m and 1-[4-(methoxycarbonyl)phenyl]-1,3-butadiene: Mitsudo T., Fischetti W., Heck R. F., J. Org. Chem., 49, 1640-1646 (1984).
    • (1984) J. Org. Chem. , vol.49 , pp. 1640-1646
    • Mitsudo, T.1    Fischetti, W.2    Heck, R.F.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.