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Volumn 39, Issue 32, 1998, Pages 5739-5742

Application of the Evans aziridination procedure to 2-substituted acrylates and cinnamates: An expedient route to α-substituted α- and β- amino acids

Author keywords

[No Author keywords available]

Indexed keywords

4 NITROPHENOL; ACETONITRILE; ACRYLIC ACID DERIVATIVE; ALPHA AMINO ACID; AZIRIDINE DERIVATIVE; BETA AMINO ACID; CINNAMIC ACID DERIVATIVE; COPPER; TOLUENE;

EID: 0032490954     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01132-0     Document Type: Article
Times cited : (55)

References (32)
  • 9
    • 0030955088 scopus 로고    scopus 로고
    • 5. For a concise review and leading references, see : Wirth, T. Angew. Chem. Int. Ed. Engl. 1997, 36, 225-227.
    • (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 225-227
    • Wirth, T.1
  • 24
    • 0010444126 scopus 로고    scopus 로고
    • note
    • 20 (900 mg, 2.4 mmol). The reaction mixture was stirred at rt for 24 h and then filtered on silica gel. The filtrate was evaporated to dryness under reduced pressure and the oily residue was purified by flash chromatography on silica gel (heptane-ethyl acetate 3:1) affording the corresponding aziridine (310 mg, 58% ; Table 1, entry 2a) as a white solid.
  • 27
    • 0010488142 scopus 로고    scopus 로고
    • note
    • 17. The lower yield of aziridine obtained with methyl acrylate and PhI=NTs (18%) compared to the results reported by Evans and coworkers (40%) (ref. 10) may be attributed to the fact that these authors used a large excess of acrylate (5 eq) with the nitrene source being the limiting reagent (1 eq). Yields were based on the latter.
  • 28
    • 0010485357 scopus 로고    scopus 로고
    • note
    • 18. All new compounds gave satisfactory analytical and spectroscopic data.


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