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Volumn , Issue 4, 2006, Pages 543-546

First 1,3-dipolar cycloaddition of azomethine ylides with (E)-ethyl 3-fluoroacrylate: Regio- and stereoselective synthesis of enantiopure fluorinated prolines

Author keywords

1,3 dipolar cycloaddition; Azomethine ylides; Fluorinated prolines; Fluoroolefins

Indexed keywords

ACRYLIC ACID DERIVATIVE; AZOMETHINE YLIDE; ETHYL 3 FLUOROACRYLATE; PROLINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 33644999409     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-933127     Document Type: Article
Times cited : (33)

References (37)
  • 1
  • 2
    • 1642336022 scopus 로고    scopus 로고
    • Gribble, G. W.; Jaule, J. A., Eds.; Pergamon: Amsterdam
    • (b) Janasik, T.; Bergman, J. In Progress in Heterocyclic Chemistry, Vol. 15; Gribble, G. W.; Jaule, J. A., Eds.; Pergamon: Amsterdam, 2003, 140.
    • (2003) Progress in Heterocyclic Chemistry , vol.15 , pp. 140
    • Janasik, T.1    Bergman, J.2
  • 5
    • 0000002236 scopus 로고
    • Padwa, A., Ed.; J. Wiley and Sons: New York
    • (c) Lawin, J. W. In 1,3-Dipolar Cycloaddition Chemistry, Vol. 1; Padwa, A., Ed.; J. Wiley and Sons: New York, 1984, 653.
    • (1984) 1,3-Dipolar Cycloaddition Chemistry , vol.1 , pp. 653
    • Lawin, J.W.1
  • 7
    • 33644999218 scopus 로고    scopus 로고
    • Kobayashi, S.; Jorgensen, K. V., Eds.; Wiley-VCH: Weinheim, Chap. 6
    • (b) Gothelf, K. V. In Cycloaddition Reaction in Organic Synthesis; Kobayashi, S.; Jorgensen, K. V., Eds.; Wiley-VCH: Weinheim, 2001, Chap. 6.
    • (2001) Cycloaddition Reaction in Organic Synthesis
    • Gothelf, K.V.1
  • 15
    • 33644994743 scopus 로고    scopus 로고
    • Ramachandran, P. V., Ed.; ACS Symposium Series: Washington, DC
    • (b) Asymmetric Fluoroorganic Chemistry; Ramachandran, P. V., Ed.; ACS Symposium Series: Washington, DC, 2000.
    • (2000) Asymmetric Fluoroorganic Chemistry
  • 16
    • 0000610760 scopus 로고
    • Hudlicky, M.; Pavlath, A. E., Eds.; ACS Monograph 187, American Chemical Society: Washington, DC
    • (c) Smart, B. E. Chemistry of Organic Fluorine Compound: A Critical Review; Hudlicky, M.; Pavlath, A. E., Eds.; ACS Monograph 187, American Chemical Society: Washington, DC, 1995, 979.
    • (1995) Chemistry of Organic Fluorine Compound: A Critical Review , pp. 979
    • Smart, B.E.1
  • 24
    • 33645015448 scopus 로고    scopus 로고
    • note
    • +].
  • 25
    • 33645007098 scopus 로고    scopus 로고
    • note
    • + + Na].
  • 26
    • 33644997384 scopus 로고    scopus 로고
    • note
    • 2-EtOAc 200:1. After column chromatography the two cycloadducts were subjected to semi-preparative HPLC separation. HPLC (hexane-i-PrOH gradient starting from 0.5% i-PrOH, to 11 min, then 1.05% i-PrOH to 25 min, then 2.25% i-PrOH). Selected data for 4a,a′.
  • 27
    • 33644992139 scopus 로고    scopus 로고
    • note
    • +].
  • 32
    • 33644992138 scopus 로고    scopus 로고
    • note
    • 5. This concatenation (trans-trans-cis) corresponds to the 2R*,3S*,4S*,5R* configuration. Analogous data were obtained for 5a′, 4a and 4a′.
  • 33
    • 33645004574 scopus 로고    scopus 로고
    • note
    • MMFF force field as implemented in Titan 1.0.5, Wavefunction, Inc. The standard conformational search was applied to 5a and 5a′, and the structures within 3 kcal/mol above the global minima were analyzed for the determination of the distances between the pyrrolidine hydrogens and the menthol hydrogens. In Figure 1 are reported the two global energy minima.
  • 35
    • 33644992272 scopus 로고    scopus 로고
    • note
    • D-17.8 (c 0.2, MeOH).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.