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Volumn 50, Issue 17, 2009, Pages 1889-1892

A practical method to access enantiopure β-perfluoroalkyl-β-amino acids: diastereoselective reduction of cyclic enamino-esters

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 2 PHENYLETHANOL; 3 AMINO 4,4,4 TRIFLUOROBUTANOIC ACID; 4,4,4 TRIFLUORO 3 OXOBUTANOATE; AMINO ACID DERIVATIVE; BETA PERFLUOROALKY BETA AMINO ACID DERIVATIVE; BUTYRIC ACID; ESTER DERIVATIVE; PHENETHYL ALCOHOL; UNCLASSIFIED DRUG;

EID: 61749093481     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.01.159     Document Type: Article
Times cited : (25)

References (39)
  • 1
    • 0003907264 scopus 로고
    • For reviews, see:. Welch J.T., and Eswarakrishnan S. (Eds), John Wiley & Sons, New York
    • For reviews, see:. In: Welch J.T., and Eswarakrishnan S. (Eds). Fluorine in Bioorganic Chemistry (1991), John Wiley & Sons, New York
    • (1991) Fluorine in Bioorganic Chemistry
  • 35
    • 33746918968 scopus 로고    scopus 로고
    • A plausible mechanism for the formation of 9 is as follows: {A figure is presented} For examples of a related rearrangement reaction, see:
    • A plausible mechanism for the formation of 9 is as follows: {A figure is presented} For examples of a related rearrangement reaction, see:. Soloshonok V.A., Ohkura H., and Yasumoto M. Mendeleev Commun. 16 (2006) 165
    • (2006) Mendeleev Commun. , vol.16 , pp. 165
    • Soloshonok, V.A.1    Ohkura, H.2    Yasumoto, M.3
  • 37
    • 61749091384 scopus 로고    scopus 로고
    • note
    • Crystallographic data for the determination of the absolute configuration of 1 has been limited to one report (Kukhar, V. P.; Soloshonok, V. A.; Švedas, V. K.; Kotik, N. V.; Galaev, I. Y.; Kirilenko, A. G.; Kozlove, E. V. Bioorgan. Khim. 1993, 19, 474). However, the assignment was based on an X-ray crystal structure of (-)-1 having neither chiral internal reference nor heavy atom indispensable for the observation of anomalous X-ray scattering. In comparison with the present result, the assignment made by Kukhar et al. was confirmed to be correct.
  • 38
    • 61749090039 scopus 로고    scopus 로고
    • note
    • As far as we know (S)-6 and (3S,5S)-7 have been deposited with the Cambridge Crystallographic Data Center as Supplementary Publication Numbers CCDC 709483 and CCDC 709484, respectively. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, by emailing data_request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.
  • 39
    • 61749089838 scopus 로고    scopus 로고
    • note
    • The cyclic enamino-ester (S)-10 was prepared from an easily available fluorinated building block (ethyl 4,4,5,5,5-pentafluoroethylpent-1-ynoate). See Ref. 11.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.