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Volumn 3, Issue 5, 2001, Pages 773-776

Asymmetric synthesis of β-substituted α-methyl-β-amino esters by mannich reaction of (S,S)-(+)-pseudoephedrine acetamide derived enolate with imines

Author keywords

[No Author keywords available]

Indexed keywords

ACETAMIDE DERIVATIVE; DRUG DERIVATIVE; EPHEDRINE; IMINE;

EID: 0035826373     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0155384     Document Type: Article
Times cited : (56)

References (73)
  • 1
    • 0003828324 scopus 로고
    • Barret, G. C., Ed.; Chapman and Hall: London, New York
    • See, for example: (a) Drey, C. N. C. In Chemistry and Biochemistry of Amino Acids; Barret, G. C., Ed.; Chapman and Hall: London, New York, 1985.
    • (1985) Chemistry and Biochemistry of Amino Acids
    • Drey, C.N.C.1
  • 10
  • 45
    • 0033523708 scopus 로고    scopus 로고
    • and references therein
    • See also: (b) Arend, M. Angew. Chem., Int. Ed. 1999, 38, 2873 and references therein.
    • (1999) Angew. Chem., Int. Ed. , vol.38 , pp. 2873
    • Arend, M.1
  • 51
    • 0000584420 scopus 로고
    • Morrison, J. D., Ed.; Academic Press: New York, Chapter 2
    • Heathcock, C. H. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, Part B, Chapter 2.
    • (1984) Asymmetric Synthesis , vol.3 , Issue.PART B
    • Heathcock, C.H.1
  • 65
    • 0041404024 scopus 로고    scopus 로고
    • note
    • 4, and filtered, and the solvent was removed in vacuo affording the wanted amides after flash column chromatography purification (hexanes:AcOEt 2:8). All amides gave physical and spectroscopic data consistent with the proposed structures.
  • 66
    • 33748229442 scopus 로고
    • For the effect of LiCl in the reaction of pseudoephedrine amide enolates, see: (a) Rück, K. Angew. Chem., Int. Ed. Engl. 1995, 34, 433.
    • (1995) Angew. Chem., Int. Ed. Engl. , vol.34 , pp. 433
    • Rück, K.1
  • 69
    • 33947335911 scopus 로고
    • 13C NMR resonance for the C=N group indicating that only one of the two possible E/Z isomers of the azomethyne 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
  • 70
    • 0041404023 scopus 로고    scopus 로고
    • note
    • 4 and filtered, and the solvent was removed in vacuo, affording the desired β-aminoesters after flash column chromatography purification (hexanes:AcOEt 1:1). All products gave physical and spectroscopic data consistent with the proposed structures.
  • 72
    • 0042907168 scopus 로고    scopus 로고
    • note
    • 1H NMR spectrum of the reaction crude showed the presence of only one diastereoisomer with respect to the relative configuration between both chiral centers. HPLC analysis under conditions optimized for racemic (±)-5a (ChiralcelOD, UV detector, n-hexane/2-propanol 95:5, 0.80 mL/min) indicated the presence of only one of the two possible ones.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.