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Volumn 13, Issue 6, 2011, Pages 1302-1305

Fluoroallylboration-olefination for the synthesis of (Z)-4,4-difluoropent- 2-enoates and 5,5-difluoro-5,6-dihydropyran-2-ones

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKENE; FLUORINATED HYDROCARBON; PYRONE DERIVATIVE;

EID: 79952603855     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol103097s     Document Type: Article
Times cited : (21)

References (35)
  • 11
  • 22
    • 0002827445 scopus 로고
    • Eliel E.L. Wilen S.H. Eds.; John Wiley & Sons, Inc.: New York
    • Vedejs, E.; Peterson, M. J. Topics in Stereochemistry; Eliel, E. L.; Wilen, S. H., Eds.; John Wiley & Sons, Inc.: New York, 1994; Vol. 21, pp 1 - 158.
    • (1994) Topics in Stereochemistry , vol.21 , pp. 1-158
    • Vedejs, E.1    Peterson, M.J.2
  • 27
    • 0000665529 scopus 로고
    • Similar low yields have been reported for the methylenation of a β-acetoxy ketone during Wittig reaction
    • Similar low yields have been reported for the methylenation of a β-acetoxy ketone during Wittig reaction: Hibino, J. I.; Okazoe, T.; Takai, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 5579
    • (1985) Tetrahedron Lett. , vol.26 , pp. 5579
    • Hibino, J.I.1    Okazoe, T.2    Takai, K.3    Nozaki, H.4
  • 31
    • 79952581692 scopus 로고    scopus 로고
    • note
    • Attempts to debenzylate the benzyloxy alcohols 1, prepared via the fluoroallylboration of benzaldehyde bearing electron-withdrawing groups, such as p -fluoro, p -chloro, and p -trifluoromethyl groups, resulted in dehalogenation along with debenzylation forming 2a, 2a, and 2c, respectively. Debenyzlation of the benzyloxy alcohol derived from p -nitrobenzaldehyde resulted in the formation of the corresponding p -amino compound, 3,3-difluoro-4-hydroxy-4-(4- aminophenyl)butan-2-one.
  • 35
    • 79952606058 scopus 로고    scopus 로고
    • note
    • 2O = 1/1) to provide δ-lactone 6a as a white solid (35 mg, 69%), mp 112-113 °C.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.