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Volumn 69, Issue 23, 2004, Pages 8168-8171

Organocatalyzed solvent-free Aza-Henry reaction: A breakthrough in the one-pot synthesis of 1,2-diamines

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYSTS; ENVIRONMENTAL IMPACT; PARAFFINS; REACTION KINETICS; REDUCTION; SOLVENTS; STOICHIOMETRY; SYNTHESIS (CHEMICAL);

EID: 8644269566     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0488762     Document Type: Article
Times cited : (75)

References (55)
  • 3
    • 0000851805 scopus 로고
    • Trost, B. M., Ed.; Pergamon: Oxford
    • (a) Rosini, G. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 2, p 321.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 321
    • Rosini, G.1
  • 41
    • 8644236221 scopus 로고    scopus 로고
    • note
    • ,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) and 1,5-diazabicyclo-[4.3.0]non- 5-ene (DBN) were equally effective in promoting the reaction.
  • 43
    • 8644288612 scopus 로고    scopus 로고
    • note
    • High diastereselectivity observed is not a result of a thermodynamic equilibration in the presence of a strong base such as TMG, as β-nitroamine 2a with a 55:45 diastereomeric ratio (obtained from a reaction catalyzed by DABCO) was recovered with the same anti/syn ratio after several hours in the presence of 5 mol % TMG.
  • 44
    • 8644253073 scopus 로고    scopus 로고
    • note
    • 2, and toluene, observing a remarkable drop in the rate of the reaction, presumably due to dilution effects.
  • 45
    • 8644261942 scopus 로고    scopus 로고
    • note
    • Other imines derived from enolizable aliphatic aldehydes were not tested in the reaction due to the lack of methods for the preparation of these compounds.
  • 55
    • 8644232970 scopus 로고    scopus 로고
    • note
    • In the one-pot protocol, 10 equiv of zinc should be used instead of 9 equiv due to the consumption of the reducing agent for excess 1-nitropropane,


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.