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Volumn , Issue 23, 2006, Pages 4065-4074

(+)-(S,S)-pseudoephedrine as a chiral auxiliary in asymmetric Mannich reactions: Scope and limitations

Author keywords

Amino acids; Asymmetric synthesis; Chiral auxiliaries; Lactams; Mannich bases

Indexed keywords

AMINO ACIDS; ESTERS; REACTION KINETICS; STEREOCHEMISTRY; SUBSTITUTION REACTIONS;

EID: 33845606246     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-950347     Document Type: Article
Times cited : (26)

References (69)
  • 3
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    • Juaristi, E.; Sholonoshok, V. A., Eds.; Wiley & Sons: New Jersey
    • (a) Enantioselective Synthesis of β-Amino Acids, 2nd ed.; Juaristi, E.; Sholonoshok, V. A., Eds.; Wiley & Sons: New Jersey, 2005.
    • (2005) Enantioselective Synthesis of β-Amino Acids, 2nd Ed.
  • 16
    • 0001059120 scopus 로고    scopus 로고
    • Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, Chap. 26.2
    • (d) Denmark, S. E.; Nicaise, O. J.-C. In Comprehensive Asymmetric Catalysis, Vol. 2; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999, Chap. 26.2.
    • (1999) Comprehensive Asymmetric Catalysis , vol.2
    • Denmark, S.E.1    Nicaise, O.J.-C.2
  • 55
    • 0032506561 scopus 로고    scopus 로고
    • The aldol reaction between propanamide 1a and benzaldehyde performed at -105 °C and in the absence of LiCl led to the formation of the corresponding adduct in 93% yield after two hours: Vicario, J. L.; Badia, D.; Dominguez, E.; Carrillo, L. Tetrahedron Lett. 1998, 39, 9267.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 9267
    • Vicario, J.L.1    Badia, D.2    Dominguez, E.3    Carrillo, L.4
  • 56
    • 33748229442 scopus 로고
    • See also
    • For the influence of LiCl in the reactivity of pseudoephedrine enolates see refs. 10a and 15a. See also: (a) Rück, K. Angew. Chem., Int. Ed. Engl. 1995, 34, 433.
    • (1995) Angew. Chem., Int. Ed. Engl. , vol.34 , pp. 433
    • Rück, K.1
  • 61
    • 33947335911 scopus 로고
    • 13C NMR resonance for the C=N group indicating that only one of the two possible E/Z isomers of the azomethine bond was present. The preference for the E-configuration in imines in which the C=N bond is conjugated with one or more aromatic rings has already been described: Hine, J.; Yeh, C. Y. J. Am. Chem. Soc. 1967, 89, 2669.
    • (1967) J. Am. Chem. Soc. , vol.89 , pp. 2669
    • Hine, J.1    Yeh, C.Y.2
  • 62
    • 0001271879 scopus 로고    scopus 로고
    • Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme: Stuttgart
    • For a discussion, see: Risch, N.; Arend, M. Houben-Weyl, 4th ed., Vol. E 21/3; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme: Stuttgart, 1996, 1833.
    • (1996) Houben-Weyl, 4th Ed. , vol.E21-3 , pp. 1833
    • Risch, N.1    Arend, M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.