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Volumn 61, Issue 16, 1996, Pages 5557-5563

Stereoselective reduction of enantiopure β-enamino esters by hydride: A convenient synthesis of both enantiopure β-amino esters

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; BETA AMINO ACID;

EID: 0029773346     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960107y     Document Type: Article
Times cited : (152)

References (60)
  • 5
    • 0003852053 scopus 로고
    • (e) Total and semi-synthetic approaches to Taxol. Tetrahedron symposia-in-print (No. 48). Tetrahedron 1992, 48, 6593.
    • (1992) Tetrahedron , vol.48 , pp. 6593
  • 9
    • 0021878444 scopus 로고
    • (a) Dürckheimer, W; Blumbach, J.; Lattrell, R.; Scheunemann, K. H. Angew. Chem. 1983, 97, 183-205; Angew. Chem., Int. Ed. Engl. 1985, 24, 180-202.
    • (1985) Angew. Chem., Int. Ed. Engl. , vol.24 , pp. 180-202
  • 16
    • 0028130028 scopus 로고
    • (a) Cole, D. C. Tetrahedron 1994, 50, 9517-9582.
    • (1994) Tetrahedron , vol.50 , pp. 9517-9582
    • Cole, D.C.1
  • 45
    • 16044367169 scopus 로고    scopus 로고
    • note
    • The absolute configuration of the β-amino esters 2b,c,d,f,i,k,m was ascertained by comparison of spectroscopic data of confrontable β-amino esters of known configuration.
  • 56
    • 16044364584 scopus 로고    scopus 로고
    • note
    • The conformations were fully explored and minimized using the MM+ force field of the Hyper Chem package, from Hyper Cube Inc., Waterloo, Ontario, Canada.
  • 57
    • 16044369225 scopus 로고
    • Kagan, H. B., Ed.; Georg Thieme Publishers: Stuttgart
    • Generally, the α- and β-amino acids rotate polarized light in the same direction of the relative methyl or ethyl esters: (a) Jacques, J.; Gros, C.; Bourcier, S. In Stereochemistry; Kagan, H. B., Ed.; Georg Thieme Publishers: Stuttgart, 1977; Vol. 4, p 107. (b) Yamada, T.; Kuwata, S.; Watanabe, H. Tetrahedron Lett. 1978, 1813.
    • (1977) Stereochemistry , vol.4 , pp. 107
    • Jacques, J.1    Gros, C.2    Bourcier, S.3
  • 58
    • 0006599511 scopus 로고
    • Generally, the α- and β-amino acids rotate polarized light in the same direction of the relative methyl or ethyl esters: (a) Jacques, J.; Gros, C.; Bourcier, S. In Stereochemistry; Kagan, H. B., Ed.; Georg Thieme Publishers: Stuttgart, 1977; Vol. 4, p 107. (b) Yamada, T.; Kuwata, S.; Watanabe, H. Tetrahedron Lett. 1978, 1813.
    • (1978) Tetrahedron Lett. , pp. 1813
    • Yamada, T.1    Kuwata, S.2    Watanabe, H.3
  • 59
    • 16044369504 scopus 로고    scopus 로고
    • note
    • The β-amino esters 3a,b,d,e, as N-1-naphthoyl derivatives, were analyzed on a S,S-Whelk 01 column (purchased from Regis Chemical Co., Morton Grove, IL), 250 × 4.6 mm i.d., hexane-isopropanol 70:30 (v/v) as eluent, UV 254 nm detector. Elution order: L before D.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.