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Volumn 13, Issue 19, 2015, Pages 5367-5371

Kinetic resolution of primary allylic amines via palladium-catalyzed asymmetric allylic alkylation of malononitriles

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; ALLYLATION; CATALYSIS; SYNTHESIS (CHEMICAL);

EID: 84929191627     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c5ob00671f     Document Type: Article
Times cited : (28)

References (77)
  • 21
    • 33646064214 scopus 로고    scopus 로고
    • ed. L. E. Overman, Wiley, Hoboken, NJ
    • L. E. Overman and N. E. Carpenter, in Organic Reactions, ed., L. E. Overman, Wiley, Hoboken, NJ, 2005, vol. 6, p. 1
    • (2005) Organic Reactions , vol.6 , pp. 1
    • Overman, L.E.1    Carpenter, N.E.2
  • 62
    • 84929187171 scopus 로고    scopus 로고
    • note
    • The reaction was not applicable to some other types of carbon nucleophiles such as dimethyl malonate, 2,4-pentanedione, ethyl cyanoacetate, acetophenone, indole, and phenylboronic acid
  • 70
    • 84929187172 scopus 로고    scopus 로고
    • note
    • Under our previous conditions but using an optically active ligand instead of the corresponding racemic one {[Pd(allyl)Cl]2 (2 mol%) and (S)-BINAP (4 mol%) in dichloromethane under nitrogen at room temperature}, 2c the reaction of racemic primary allylic amine rac-1a with malononitrile 2a gave malononitrile 4a in 35% yield and 64% ee together with the recovered enantioenriched primary allylic amine 1a in 55% yield and 42% ee, corresponding to an s factor of 6.8 for the kinetic resolution
  • 71
    • 84929187173 scopus 로고    scopus 로고
    • note
    • In each case the α-product was separated from the γ-product by silica gel chromatography For catalytic asymmetric allylation of ketones with racemic tertiary allylic amines, see


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.