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Volumn 17, Issue 15, 2006, Pages 2306-2310

Enantioselective synthesis of methyl-5(R)-fluorohept-6-ynoate

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; FLUORINE DERIVATIVE; KETONE; METHYL 5(R) FLUOROHEPT 6 YNOATE; SOLVENT; UNCLASSIFIED DRUG;

EID: 33748710818     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2006.08.010     Document Type: Article
Times cited : (17)

References (25)
  • 1
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    • See, for instance: (a) Hudlicky, M.; Pavlath, A. E. Chemistry of Organic Fluorine Compounds II: A Critical Review; ACS Monograph 187: Washington, DC, 1995.
  • 3
    • 0023237559 scopus 로고
    • See, for instance:
    • See, for instance:. Welch J.T. Tetrahedron 43 (1987) 3123
    • (1987) Tetrahedron , vol.43 , pp. 3123
    • Welch, J.T.1
  • 5
    • 33748699627 scopus 로고    scopus 로고
    • Ojima, I.; McCarthy, J. R.; Welch, J. T. Biomedical Frontiers in Fluorine Chemistry; Ojima, I., Ed.; ACS Symposium Series 639: Washington, DC, 1996 and references cited therein.
  • 6
    • 0036119159 scopus 로고    scopus 로고
    • For a recent review on naturally occurring fluorinated fatty acids, their analogues and derivatives see:
    • For a recent review on naturally occurring fluorinated fatty acids, their analogues and derivatives see:. Dembitsky V.M., and Srebnik M. Prog. Lipid Res. 41 (2002) 315
    • (2002) Prog. Lipid Res. , vol.41 , pp. 315
    • Dembitsky, V.M.1    Srebnik, M.2
  • 7
    • 16444381982 scopus 로고    scopus 로고
    • for a recent review on the fluorinated analogues of fatty acids and their acyclic metabolites see:
    • for a recent review on the fluorinated analogues of fatty acids and their acyclic metabolites see:. Prakesch M., Grée D., Chandrasekhar S., and Grée R. Eur. J. Org. Chem. (2005) 1221
    • (2005) Eur. J. Org. Chem. , pp. 1221
    • Prakesch, M.1    Grée, D.2    Chandrasekhar, S.3    Grée, R.4
  • 8
    • 33646389079 scopus 로고    scopus 로고
    • Soloshonok V.A. (Ed), ACS Publications Division and Oxford University Press, Washington, DC p 173
    • Prakesch M., Grée D., and Grée R. In: Soloshonok V.A. (Ed). Fluorine Containing Synthons (2005), ACS Publications Division and Oxford University Press, Washington, DC p 173
    • (2005) Fluorine Containing Synthons
    • Prakesch, M.1    Grée, D.2    Grée, R.3
  • 13
    • 0026716057 scopus 로고
    • The enantiomers of alcohol 4 have been obtained by several routes, including the reduction of the corresponding propargylic ketone by biotransformation, see:
    • The enantiomers of alcohol 4 have been obtained by several routes, including the reduction of the corresponding propargylic ketone by biotransformation, see:. Treilhou M., Fauve A., Pougny J.-R., Promé J.-C., and Veschambre H. J. Org. Chem. 57 (1992) 3203
    • (1992) J. Org. Chem. , vol.57 , pp. 3203
    • Treilhou, M.1    Fauve, A.2    Pougny, J.-R.3    Promé, J.-C.4    Veschambre, H.5
  • 15
    • 1642277252 scopus 로고    scopus 로고
    • and references cited therein
    • Nomura I., and Mukai C. J. Org. Chem. 69 (2004) 1803 and references cited therein
    • (2004) J. Org. Chem. , vol.69 , pp. 1803
    • Nomura, I.1    Mukai, C.2
  • 16
    • 0027534359 scopus 로고
    • and references cited therein
    • Muzart J. Synthesis (1993) 11 and references cited therein
    • (1993) Synthesis , pp. 11
    • Muzart, J.1
  • 23
    • 33748692287 scopus 로고    scopus 로고
    • note
    • However, it should be pointed out that at -20 °C, the yield of (+)-6 becomes slightly lower (50%) while larger quantities of enynes 7 are obtained.
  • 24
    • 0033609839 scopus 로고    scopus 로고
    • The (R)-absolute configuration of (+)-6 was assigned by analogy with our previous work on the DAST mediated fluorination reactions performed both on a propargylic alcohol (occurring with inversion of configuration) and the corresponding cobalt-carbonyl complex (fluorination with overall retention of configuration) see:
    • The (R)-absolute configuration of (+)-6 was assigned by analogy with our previous work on the DAST mediated fluorination reactions performed both on a propargylic alcohol (occurring with inversion of configuration) and the corresponding cobalt-carbonyl complex (fluorination with overall retention of configuration) see:. Grée D., Madiot V., and Grée R. Tetrahedron Lett. 40 (1999) 6399
    • (1999) Tetrahedron Lett. , vol.40 , pp. 6399
    • Grée, D.1    Madiot, V.2    Grée, R.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.