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Volumn 75, Issue 3, 2010, Pages 611-620

Access to α-substituted amino acid derivatives via 1,3-dipolar cycloaddition of α-amino ester derived nitrones

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVES; AMINO ESTERS; CHEMICAL EQUATIONS; CYCLOADDITION REACTION; DIPOLAR CYCLOADDITIONS; FUNCTIONALIZED; KETO ESTER; NITRONES; QUATERNARY CENTERS; SOLVENT FREE CONDITIONS; VINYL ETHERS;

EID: 75749087592     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo902107j     Document Type: Article
Times cited : (48)

References (50)
  • 8
    • 0004101860 scopus 로고
    • For reviews of cycloaddition of nitrones, see: (a) Padwa, A, Ed, Wiley-Interscience: New York, Vols
    • For reviews of cycloaddition of nitrones, see: (a) Padwa, A.; Ed. In 1,3-Dipolar Cycloaddition Chemistry; Wiley-Interscience: New York, 1984; Vols. 1-2.
    • (1984) 1,3-Dipolar Cycloaddition Chemistry , vol.1-2
  • 11
    • 0001460582 scopus 로고
    • Trost, B. M, Fleming, I, Eds, Pergamon Press: Oxford
    • (d) Little, R. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I.; Eds.; Pergamon Press: Oxford, 1991; Vol 5, pp 239-270.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 239-270
    • Little, R.D.1
  • 19
    • 0003405157 scopus 로고    scopus 로고
    • 3rd ed, Thieme, Stutgart, and references therein
    • (b) Kocienski, P. J. Protecting Groups, 3rd ed.; Thieme, Stutgart, 2004; pp 77-93 and references therein.
    • (2004) Protecting Groups , pp. 77-93
    • Kocienski, P.J.1
  • 24
    • 75749122413 scopus 로고    scopus 로고
    • Chen, Y.; L.; Leguijt, R.; Redlich, H.; Fröhlich, R. Synthesis 2006, 421.
    • (b) Chen, Y.; L.; Leguijt, R.; Redlich, H.; Fröhlich, R. Synthesis 2006, 421.
  • 33
    • 75749148944 scopus 로고    scopus 로고
    • 3 were observed for each nitrone. No NOESY correlation corresponding to the Z-isomer could be seen.
    • 3 were observed for each nitrone. No NOESY correlation corresponding to the Z-isomer could be seen.
  • 34
    • 75749137907 scopus 로고    scopus 로고
    • See Scheme 1 (adduct 3) and Table 1, entry 8 (adduct 8h).
    • See Scheme 1 (adduct 3) and Table 1, entry 8 (adduct 8h).
  • 46
    • 75749154604 scopus 로고    scopus 로고
    • Reaction was followed on the basis of the disappearance of the characteristic blue color of the SmI2 in THF. No color change was observed after 24 h, and the adduct 3a could be recovered unchanged
    • 2 in THF. No color change was observed after 24 h, and the adduct 3a could be recovered unchanged.
  • 48
    • 75749120384 scopus 로고    scopus 로고
    • Preliminary results in this field involving 1,3-DC of chiral enol ethers or alternatively 1,3-DC of chiral aspartic nitrones has been already reported in this series see ref 6
    • Preliminary results in this field involving 1,3-DC of chiral enol ethers or alternatively 1,3-DC of chiral aspartic nitrones has been already reported in this series (see ref 6).


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