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Volumn 43, Issue 25, 2004, Pages 3314-3317

Kinetic resolution of amines: A highly enantioselective and chemoselective acetylating agent with a unique solvent-induced reversal of stereoselectivity

Author keywords

Acylation; Enantioselectivity; Kinetic resolution; Solvent effects

Indexed keywords

ACETYLATION; OPTIMIZATION; SOLVENTS;

EID: 4544318236     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200453956     Document Type: Article
Times cited : (103)

References (33)
  • 7
    • 85050296727 scopus 로고    scopus 로고
    • Selectivity factor s = (rate of fast-reacting enantiomer)/(rate of slow-reacting enantiomer); for a review of kinetic resolution, see: H. B. Kagan, J. C. Fiaud, Top. Stereochem. 1998, 18, 249.
    • (1998) Top. Stereochem. , vol.18 , pp. 249
    • Kagan, H.B.1    Fiaud, J.C.2
  • 24
    • 4544303059 scopus 로고    scopus 로고
    • note
    • The kinetic resolution of (±)-1-naphthylethylamine was obtained with up to 48% ee using 0.25 equivalents of chiral reagent at room temperature. This ee value corresponds to a selectivity factor (s) of 3 at 25% conversion.
  • 27
    • 4544282211 scopus 로고    scopus 로고
    • note
    • Under these reaction conditions, Fu and co-workers achieved the kinetic resolution of (±)-1 phenylethylamine with 87% ee.
  • 29
    • 0035825126 scopus 로고    scopus 로고
    • S. Arai, S. Bellemin-Laponnaz, G. C. Fu, Angew. Chem. 2001, 113, 667; Angew. Chem. Int. Ed. 2001, 40, 234.
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 234
  • 30
    • 4544283765 scopus 로고    scopus 로고
    • note
    • This ee value corresponds to a selectivity factor (s) of 13 at 35% conversion.
  • 31
    • 0000341815 scopus 로고    scopus 로고
    • For a review on chiral 1,2-diamines, see: D. Lucet, T. Le Gall, C. Mioskowski, Angew. Chem. 1998, 110, 2724; Angew. Chem. Int. Ed. 1998, 37, 2580.
    • (1998) Angew. Chem. , vol.110 , pp. 2724
    • Lucet, D.1    Le Gall, T.2    Mioskowski, C.3
  • 32
    • 0032538362 scopus 로고    scopus 로고
    • For a review on chiral 1,2-diamines, see: D. Lucet, T. Le Gall, C. Mioskowski, Angew. Chem. 1998, 110, 2724; Angew. Chem. Int. Ed. 1998, 37, 2580.
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 2580


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.