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Volumn 9, Issue 6, 2007, Pages 1001-1004

Organocatalytic sequential α-amination-Horner-Wadsworth-Emmons olefination of aldehydes: Enantioselective synthesis of γ-amino-α, β-unsaturated esters

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRROLIDINONE; 2 PYRROLIDONE DERIVATIVE; 2-PYRROLIDONE; ALDEHYDE; ALKALOID; ALKENE; AMINE; ESTER; UNCLASSIFIED DRUG;

EID: 33947600101     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol063012j     Document Type: Article
Times cited : (80)

References (63)
  • 27
    • 85004872164 scopus 로고    scopus 로고
    • α-Amino aldehydes are often susceptible to racemization: (a) Fehrentz, J. A.; Castro, B. Synthesis 1983, 676.
    • α-Amino aldehydes are often susceptible to racemization: (a) Fehrentz, J. A.; Castro, B. Synthesis 1983, 676.
  • 33
    • 33947604066 scopus 로고    scopus 로고
    • List, B, Bolm, C, Eds
    • (d) List, B., Bolm, C., Eds. Adv. Synth. Catal. 2004, 346.
    • (2004) Adv. Synth. Catal , pp. 346
  • 44
    • 0037043180 scopus 로고    scopus 로고
    • For a review of proline-catalyzed asymmetric reactions, see
    • (c) For a review of proline-catalyzed asymmetric reactions, see: List, B. Tetrahedron 2002, 58, 5573.
    • (2002) Tetrahedron , vol.58 , pp. 5573
    • List, B.1
  • 56
    • 33947593924 scopus 로고    scopus 로고
    • General experimental procedure: To a cooled solution of dibenzyl azodicarboxylate (DBAD, 328 mg, 1 mmol) and L-proline (11.5 mg, 10 mol , in dry CH3CN (10 mL) at 0°C was added n-butyraldehyde (87 mg, 1.2 mmol, and the mixture was stirred for 2 h at 0°C and further at 10°C for 1 h. This was followed by addition of lithium bromide (130 mg, 1.5 mmol, triethyl phosphonoacetate (336 mg, 1.5 mmol, and DBU (152 mg, 1 mmol) in that sequence, and the whole mixture was stirred at 5°C for 45 min. It was then quenched by the addition of aqueous ammonium chloride solution and extracted with ethyl acetate (3 x 20 mL, The combined organic layers were washed with brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure to give the crude product 3a, which was then purified by flash column chromatography (packed with silica gel 60-120 mesh) using petroleum ether and ethyl acetate as eluents to afford the pure product
    • 6: C, 65.44; H, 6.41; N, 6.36. Found: C, 65.25; H, 6.28; N, 6.59%.
  • 59
    • 0003655764 scopus 로고    scopus 로고
    • Cordell, G. A, Ed, Academic Press: San Diego
    • (b) The Alkaloids: Chemistry and Biology; Cordell, G. A., Ed.; Academic Press: San Diego, 2000; Vol. 54.
    • (2000) The Alkaloids: Chemistry and Biology , vol.54
  • 63
    • 33947586091 scopus 로고    scopus 로고
    • 5. (Chemical Equation Presented)
    • 5. (Chemical Equation Presented)


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