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Volumn 47, Issue 27, 2006, Pages 4615-4618

Highly efficient trialkylsilylcyanation of aldehydes, ketones and imines catalyzed by a nucleophilic N-heterocyclic carbene

Author keywords

Cyanation; N Heterocyclic carbene

Indexed keywords

ALDEHYDE; IMINE; KETONE; SILANE DERIVATIVE;

EID: 33744545803     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.04.141     Document Type: Article
Times cited : (63)

References (76)
  • 8
    • 0030920183 scopus 로고    scopus 로고
    • For recent representative papers, see:
    • For recent representative papers, see:. Gerhard A.U., and Leeper F.J. Tetrahedron Lett. 38 (1997) 3615
    • (1997) Tetrahedron Lett. , vol.38 , pp. 3615
    • Gerhard, A.U.1    Leeper, F.J.2
  • 23
    • 3042770459 scopus 로고    scopus 로고
    • Recently, some communications describing the related esterifications and lactonizations catalyzed by N-heterocyclic carbenes have been reported:
    • Recently, some communications describing the related esterifications and lactonizations catalyzed by N-heterocyclic carbenes have been reported:. Chow K.Y.-K., and Bode J.W. J. Am. Chem. Soc. 126 (2004) 8126
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 8126
    • Chow, K.Y.-K.1    Bode, J.W.2
  • 32
    • 33744506545 scopus 로고    scopus 로고
    • Song, J. J.; Gallou, F.; Reeves, J. T.; Tan, Z.; Yee, N. K.; Senanayake, C. H. J. Org. Chem.2006, ASAP.
  • 70
    • 33744532551 scopus 로고    scopus 로고
    • note
    • General procedure for the preparation of N-heterocyclic carbene catalyst: A solution of 1,3-dicyclohexylimidazolium tetrafluoroborate (3.2 mg, 0.01 mmol) in freshly distilled THF (5 mL) was carefully degassed with argon at -78 °C. To the solution was added a 1.0 M THF solution of potassium tert-butoxide (10 μL, 0.01 mmol) dropwise at room temperature. After being stirred for 0.5 h, the catalyst solution was used for the following reactions without further purification.
  • 71
    • 33744505109 scopus 로고    scopus 로고
    • note
    • 4 and concentrated under vacuum. The residue was purified by column chromatography on silica gel (cooled by dry ice) (ethyl acetate/hexane = 1:50-1:10 as eluent) to give the corresponding cyanohydrin trimethylsilyl ether.
  • 73
    • 33744542790 scopus 로고    scopus 로고
    • note
    • +).
  • 74
    • 33744534189 scopus 로고    scopus 로고
    • note
    • None of these results were mentioned in the previous paper, see Ref. 11.
  • 75
    • 33744519593 scopus 로고    scopus 로고
    • note
    • +).
  • 76
    • 33744525092 scopus 로고    scopus 로고
    • note
    • +).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.