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Volumn , Issue 9, 2008, Pages 1305-1308

Asymmetric synthesis of (trifluoromethyl)piperidines: Preparation of highly enantioenriched α′-(trifluoromethyl)pipecolic acids

Author keywords

Cyclic amino acids; Fluorine; Intramolecular Mannich reaction; Piperidines; Stereoselectivity

Indexed keywords

PIPECOLIC ACID DERIVATIVE; PIPERIDINE DERIVATIVE;

EID: 45749091852     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1072768     Document Type: Article
Times cited : (16)

References (36)
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    • 3).
    • 3).
  • 23
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    • For a recent review concerning pipecolic acids and derivatives, see
    • For a recent review concerning pipecolic acids and derivatives, see: Kadouri-Puchot, C.; Comesse, S. Amino Acids 2005, 29, 101.
    • (2005) Amino Acids , vol.29 , pp. 101
    • Kadouri-Puchot, C.1    Comesse, S.2
  • 24
    • 3142782003 scopus 로고    scopus 로고
    • For a recent review concerning fluorinated amino acids, see: a
    • For a recent review concerning fluorinated amino acids, see: (a) Qiu, X.-L.; Meng, W.-D.; Qing, F.-L. Tetrahedron 2004, 60, 6711.
    • (2004) Tetrahedron , vol.60 , pp. 6711
    • Qiu, X.-L.1    Meng, W.-D.2    Qing, F.-L.3
  • 26
    • 0141833589 scopus 로고    scopus 로고
    • For approaches to racemic Tfm-pipecolic acids, see ref. 4h and: (a) Kobelkova, N. M.; Osipov, S. N.; Kolomiets, A. F. Russ. Chem. Bull. 2002, 51, 1298.
    • For approaches to racemic Tfm-pipecolic acids, see ref. 4h and: (a) Kobelkova, N. M.; Osipov, S. N.; Kolomiets, A. F. Russ. Chem. Bull. 2002, 51, 1298.
  • 28
  • 30
    • 45749094506 scopus 로고    scopus 로고
    • For 4-oxo-pipecolic acid, see: a, 11
    • For 4-oxo-pipecolic acid, see: (a) Ref. 11.
    • Ref1
  • 32
    • 33746058243 scopus 로고    scopus 로고
    • and references cited therein. For 4-hydroxy-pipecolic acid, see ref. 11 and: a
    • For 4-hydroxy-pipecolic acid, see ref. 11 and: (a) Cordero, F. M.; Bonollo, S.; Machetti, F.; Brandi, A. Eur. J. Org. Chem. 2006, 3235; and references cited therein.
    • (2006) Eur. J. Org. Chem , pp. 3235
    • Cordero, F.M.1    Bonollo, S.2    Machetti, F.3    Brandi, A.4
  • 36
    • 45749130516 scopus 로고    scopus 로고
    • Selected Data for Compounds 20, 22, and 23, 2S,6R)-6-Trifluoromethyl-pipecolic Acid (20) White solid; mp 118°C; [α]D25 -11.2 (c 1.00, MeOH, 1H NMR (400 MHz, D2O, δ, 3.61 (m, 1 H, 3.37 (dd, J, 12, 3 Hz, 1 H, 2.11 (m, 1 H, 2.06-1.95 (m, 2 H, 1.65-1.37 (m, 3 H, 13C NMR (100 MHz, D2O, δ, 177.2, 124.6 (q, JCF, 277 Hz, 60.3, 56.7 (q, JCF, 30 Hz, 27.4, 22.5, 22.0. 19F NMR (376 MHz, CD3OD, δ, 78.0. HRMS: m/z calcd for C7H11F 3NO2 [M, H, 198.0742; found: 198.0724, 2S,6R)-4,4-Dihydroxy-6-trifluoromethyl- pipecolic Acid (22) White solid; mp 95°C; [α]D 25 -2.1 (c 1.00, MeOH, 1H NMR 400 MHz, D 2O, δ
    • +]: 214.0691; found: 214.0700.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.