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Volumn 41, Issue 16, 2000, Pages 2851-2854

Diastereoselective amination of vinylic sulfoximines: Application to the asymmetric synthesis of functionalized β-substituted and β,β-disubstituted β-amino acids, and of γ-amino alcohols

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL; BETA AMINO ACID; OXIME; SULFOXIMINE; UNCLASSIFIED DRUG;

EID: 0034655818     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00307-5     Document Type: Article
Times cited : (16)

References (34)
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    • For leading references, see: Seebach, D.; Matthews, J. L. Chem. Commun. 1997, 2015. Gellman, S. H. Acc. Chem. Res. 1998, 31, 173.
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    • Gais, H.-J.; Müller, H.; Decker, J.; Hainz, R. Tetrahedron Lett. 1995, 36, 7433. Gais, H.-J.; Hainz, R.; Müller, H.; Bruns, P.; Giesen, N.; Nienstedt, S.; Raabe, G.; Runsink, J.; Decker, J.; Schleusner, M.; Hachtel, J.; Loo, R.; Woo, C.-W.; Das, P. Eur. J. Org. Chem., submitted for publication.
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    • Gais, H.-J.1    Müller, H.2    Decker, J.3    Hainz, R.4
  • 20
    • 0343386689 scopus 로고    scopus 로고
    • (a) Isolated as a mixture of Z-2b and E-2b in a ratio of 3:l
    • (a) Isolated as a mixture of Z-2b and E-2b in a ratio of 3:l.
  • 21
    • 0342951288 scopus 로고    scopus 로고
    • (b) A mixture of Z-2b and E-2b in a ratio of 3:l was used
    • (b) A mixture of Z-2b and E-2b in a ratio of 3:l was used.
  • 22
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    • and earlier work cited therein.
    • Hirama, M.; Itô, S. Heterocycles 1989, 28, 1229 and earlier work cited therein.
    • (1989) Heterocycles , vol.28 , pp. 1229
    • Hirama, M.1    Itô, S.2
  • 23
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    • 2): 3a: +130.5 (c 0.55); 3b: +179.1 (c 0.45); 6: +89.3 (c 0.70); 8: +51.4 (c 0.70); 9: +49.3 (c 0.15); 10: +23.3 (c 0.24); 12: +140.4 (c 0.29); 13: +81.2 (c 1.05); 14: +134.0 (c 0.70); 15: -44.7 (c 0.55); 16: -28.0 (c 0.69); 17: -37.3 (c 0.23)
    • 2): 3a: +130.5 (c 0.55); 3b: +179.1 (c 0.45); 6: +89.3 (c 0.70); 8: +51.4 (c 0.70); 9: +49.3 (c 0.15); 10: +23.3 (c 0.24); 12: +140.4 (c 0.29); 13: +81.2 (c 1.05); 14: +134.0 (c 0.70); 15: -44.7 (c 0.55); 16: -28.0 (c 0.69); 17: -37.3 (c 0.23).
  • 24
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    • For the addition of N-nucleophiles to vinylic sulfoximines, see: (a)
    • For the addition of N-nucleophiles to vinylic sulfoximines, see: (a) Annunziata, R.; Cinquini, M. J. Chem. Soc., Perkin Trans. 1 1979, 1684.
    • (1979) J. Chem. Soc., Perkin Trans. , vol.1 , pp. 1684
    • Annunziata, R.1    Cinquini, M.2
  • 26
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    • (c)
    • (c) Reggelin, M.; Heinrich, T. Angew. Chem. 1998, 110, 3005; Angew. Chem., Int. Ed. Engl. 1998, 37, 2883.
    • (1998) Angew. Chem. , vol.110 , pp. 3005
    • Reggelin, M.1    Heinrich, T.2
  • 27
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    • (c) Reggelin, M.; Heinrich, T. Angew. Chem. 1998, 110, 3005; Angew. Chem., Int. Ed. Engl. 1998, 37, 2883.
    • (1998) Angew. Chem., Int. Ed. Engl. , vol.37 , pp. 2883
  • 29
    • 0342517063 scopus 로고    scopus 로고
    • For the asymmetric synthesis of functionalized pyrrolidines from sulfoximines of type C carrying an amino group at the β′-position and a chiral substituent at the N atom, see: Ref 13c.
    • For the asymmetric synthesis of functionalized pyrrolidines from sulfoximines of type C carrying an amino group at the β′-position and a chiral substituent at the N atom, see: Ref 13c.
  • 32
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    • Crystallographic data for the structures of 12 and 10 have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC-140587 and CCDC-140588. Copies of the data can be obtained free of charge on application, supplying the full journal reference, to: The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK.
    • Crystallographic data for the structures of 12 and 10 have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC-140587 and CCDC-140588. Copies of the data can be obtained free of charge on application, supplying the full journal reference, to: The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK.
  • 34
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    • All new compounds were fully characterized including elemental analysis.
    • All new compounds were fully characterized including elemental analysis.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.