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Volumn 50, Issue 16, 2009, Pages 1844-1846

One-pot synthesis of α-aminonitriles from alkyl and aryl cyanides: a Strecker reaction via aldimine alanes

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE CYANOHYDRIN; ALPHA METHYLBENZYLAMINE; ALUMINUM DERIVATIVE; CYANIDE; CYANOHYDRIN; DIISOBUTYLALUMINIUM HYDRIDE; IMINE; NITRILE; NUCLEOPHILE; TRIETHYLAMINE; UNCLASSIFIED DRUG;

EID: 61349167157     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.02.004     Document Type: Article
Times cited : (32)

References (20)
  • 6
    • 0041378065 scopus 로고    scopus 로고
    • Groger H. Chem. Rev. 103 (2003) 2795-2827
    • (2003) Chem. Rev. , vol.103 , pp. 2795-2827
    • Groger, H.1
  • 15
    • 61349164946 scopus 로고    scopus 로고
    • note
    • General procedure for the preparation of 3: Diisobutylaluminium hydride (1.4 equiv, 2.8 mmol, 1 M in dichloromethane) was added to the nitrile (1 mmol) in dichloromethane (5 mL) under argon at -78 °C. The mixture was stirred for 30 min and the excess DIBAL-H was quenched by the addition of ethyl acetate (0.4 mmol) at -78 °C. After 5 min, catalytic triethylamine (0.1 equiv, 0.1 mmol) and (S)-(-)-1-phenylethylamine (5 equiv, 5 mmol) were added, and the mixture was stirred for 2 h at dry ice temperature. Next, acetone cyanohydrin (10 equiv, 10 mmol) was added via syringe and the temperature was allowed to warm to 20 °C and the mixture was stirred overnight. After dilution with dichloromethane (10 mL), the solution was washed with 1 N sodium hydroxide (10 mL). The organic layer was dried over magnesium sulfate and the solvent was removed in vacuum. The residue was purified by column chromatography on silica gel using hexane/ethyl acetate as eluent (93/7-9/1).


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