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Volumn 64, Issue 10, 2008, Pages 2419-2424

Unusual reactions of Grignard reagents toward fluoroalkylated esters

Author keywords

Fluoroalkyl groups; Grignard reagents; Meerwein Ponndorf Verley reductions

Indexed keywords

ALKYL GROUP; ESTER DERIVATIVE; GRIGNARD REAGENT; KETONE DERIVATIVE; MAGNESIUM DERIVATIVE;

EID: 38649132286     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.01.015     Document Type: Article
Times cited : (36)

References (34)
  • 14
    • 33947462538 scopus 로고
    • When ethyl trichloroacetate was added to an ethereal solution of PhMgBr (4 equiv) at 0 °C and then refluxing for 1.5 h furnished an almost quantitative amount of PhCl, see:
    • When ethyl trichloroacetate was added to an ethereal solution of PhMgBr (4 equiv) at 0 °C and then refluxing for 1.5 h furnished an almost quantitative amount of PhCl, see:. Kaluszyner A., and Reuter S. J. Am. Chem. Soc. 75 (1953) 5126
    • (1953) J. Am. Chem. Soc. , vol.75 , pp. 5126
    • Kaluszyner, A.1    Reuter, S.2
  • 15
    • 38649098512 scopus 로고    scopus 로고
    • note
    • In Ref. 2, Creary reported basically identical result for the reaction of PhMgBr and ethyl acetate in ether at -78 °C, followed by warming to rt leading to the exclusive formation of the tertiary alcohol 1,1-diphenylethanol in 96% yield.
  • 16
    • 0002204826 scopus 로고
    • For the MPV reductions using fluorine-containing substrates, see:. Fleming I., and Trost B.M. (Eds), Pargamon, Oxford
    • For the MPV reductions using fluorine-containing substrates, see:. Kellogg R.M. In: Fleming I., and Trost B.M. (Eds). Comprehensive Organic Synthesis (1991), Pargamon, Oxford 88
    • (1991) Comprehensive Organic Synthesis , pp. 88
    • Kellogg, R.M.1
  • 20
    • 38649084130 scopus 로고    scopus 로고
    • note
    • Although this yield should be theoretically zero, a small amount of contaminant might cause this reaction.
  • 23
    • 0035801609 scopus 로고    scopus 로고
    • 13C NMR chemical shifts of 3a (δ 179.59 (q, J=34 Hz)) and 3e (δ 197.94), clearly indicating more deshielded circumstance of the carbonyl carbon atom of 3e, see:
    • 13C NMR chemical shifts of 3a (δ 179.59 (q, J=34 Hz)) and 3e (δ 197.94), clearly indicating more deshielded circumstance of the carbonyl carbon atom of 3e, see:. Asao N., Asano T., and Yamamoto Y. Angew. Chem., Int. Ed. 40 (2001) 3206
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 3206
    • Asao, N.1    Asano, T.2    Yamamoto, Y.3
  • 25
    • 38649107867 scopus 로고    scopus 로고
    • note
    • A small amount of the aldol product (ca. 5% yield) was also detected in the case of trifluorinated case. The similar situation was occurred for the related system in Ref. 7b.
  • 27
    • 38649095260 scopus 로고    scopus 로고
    • note
    • -1 for 13e.
  • 29
    • 36649036322 scopus 로고    scopus 로고
    • Moreover, Oppenauer oxidation by using the high electrophilicity of trifluoroacetone was also reported.
    • Moreover, Oppenauer oxidation by using the high electrophilicity of trifluoroacetone was also reported. Mello R., Martínez-Ferrer J., Asensio G., and González-Núñez M.E. J. Org. Chem. 72 (2007) 9376
    • (2007) J. Org. Chem. , vol.72 , pp. 9376
    • Mello, R.1    Martínez-Ferrer, J.2    Asensio, G.3    González-Núñez, M.E.4
  • 32
    • 38649121503 scopus 로고    scopus 로고
    • Kitazume, T.; Takeda, M. Jpn. Kokai Tokkyo Koho JP 01233244, 1989.
    • Kitazume, T.; Takeda, M. Jpn. Kokai Tokkyo Koho JP 01233244, 1989.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.