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Volumn , Issue 11, 2005, Pages 1731-1733

A simple stereoselective access to α-trifluoromethylated piperidines

Author keywords

Diastereoselectivity; Fluorine; Intramolecular Mannich reaction; Piperidines

Indexed keywords

HETEROCYCLIC COMPOUND; PIPERIDINE DERIVATIVE;

EID: 22244434604     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-871552     Document Type: Article
Times cited : (7)

References (26)
  • 4
    • 0036882589 scopus 로고    scopus 로고
    • and references cited therein
    • Ismail, F. M. D. J. Fluorine Chem. 2002, 118, 27; and references cited therein.
    • (2002) J. Fluorine Chem. , vol.118 , pp. 27
    • Ismail, F.M.D.1
  • 10
    • 0034595676 scopus 로고    scopus 로고
    • For a review concerning monotrifluoromethylated saturated cycles, see: Lin, P.; Jiang, J. Tetrahedron 2000, 56, 3635.
    • (2000) Tetrahedron , vol.56 , pp. 3635
    • Lin, P.1    Jiang, J.2
  • 11
    • 22244491802 scopus 로고    scopus 로고
    • note
    • For representative examples of α-trifluoromethyl piperidines and piperideines preparation, see: (a) Ref. 7
  • 20
    • 0346025405 scopus 로고    scopus 로고
    • For successful application of our methodology in the enantioselective synthesis of an indolizidine alkaloid, see: Davis, F. A.; Yang, B. Org. Lett. 2003, 5, 5011.
    • (2003) Org. Lett. , vol.5 , pp. 5011
    • Davis, F.A.1    Yang, B.2
  • 24
    • 22244488562 scopus 로고    scopus 로고
    • note
    • 3 (10 mL) was added and the keto-protected piperidone extracted with ethyl acetate (4 × 30 mL). The combined organic extracts were dried, filtered, and concentrated. The residue was purified by column chromatography using ethyl acetate-cyclohexane as eluent.
  • 25
    • 22244486494 scopus 로고    scopus 로고
    • note
    • The low yield is due to partial butanal aldol condensation prior to cyclization, leading to a complex reaction mixture.
  • 26
    • 22244487811 scopus 로고    scopus 로고
    • note
    • All new compounds are fully characterized.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.