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Volumn 67, Issue 17, 2011, Pages 3091-3097

Exploiting morph-DAST mediated ring-expansion of substituted cyclic β-amino alcohols for the preparation of cyclic fluorinated amino acids. Synthesis of 5-fluoromethylproline and 5-fluoropipecolic acid

Author keywords

Amino acids; Fluorine; Morph DAST; Pipecolic acid; Proline

Indexed keywords

5 FLUOROMETHYLPROLINE; 5 FLUOROPIPECOLIC ACID; AMINO ACID; AMINO ACID DERIVATIVE; AMINOALCOHOL; FLUORINE DERIVATIVE; MORPHOLINOSULFUR TRIFLUORIDE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 79953725104     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2011.02.082     Document Type: Article
Times cited : (26)

References (62)
  • 6
    • 79953722011 scopus 로고    scopus 로고
    • An MDL Discovery Gate search in October 2010 revealed that 111 derivatives of 4-fluoroproline were in clinical trials
    • An MDL Discovery Gate search in October 2010 revealed that 111 derivatives of 4-fluoroproline were in clinical trials.
  • 37
    • 79953676648 scopus 로고    scopus 로고
    • During this work, the synthesis of a derivative of 1a was mentioned in Uoto, K.; Kawato, H.; Sugimoto, Y.; Naito, H.; Miyazaki, M.; Taniguchi, T.; Aonuma, M. WO2009151, A1 20091217. The patent, however, is written in Japanese, and no detailed analytical data for the obtained compounds are given
    • During this work, the synthesis of a derivative of 1a was mentioned in Uoto, K.; Kawato, H.; Sugimoto, Y.; Naito, H.; Miyazaki, M.; Taniguchi, T.; Aonuma, M. WO2009151, A1 20091217. The patent, however, is written in Japanese, and no detailed analytical data for the obtained compounds are given.
  • 38
    • 79953707675 scopus 로고    scopus 로고
    • Morph-DAST was preferred over DAST as a result of its higher thermal stability and better yields of fluorinated products in certain cases:
    • Morph-DAST was preferred over DAST as a result of its higher thermal stability and better yields of fluorinated products in certain cases:
  • 43
    • 79953683770 scopus 로고    scopus 로고
    • The transformation of N-benzylprolinol into N-benzyl-2- fluoromethylpyrrolidine is described in
    • The transformation of N-benzylprolinol into N-benzyl-2- fluoromethylpyrrolidine is described in
  • 52
    • 11444266887 scopus 로고    scopus 로고
    • Rearrangement of 2-hydroxypyrrolidines into 3-fluoropiperidines is described in: (a) C. Ye, and J.M. Shreeve J. Fluorine Chem. 125 2004 1869
    • (2004) J. Fluorine Chem. , vol.125 , pp. 1869
    • Ye, C.1    Shreeve, J.M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.