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Volumn 3, Issue 5, 2001, Pages 743-746

Mesyloxy-group migration as the stereoselective preparation method of various functionalized olefins and its reaction mechanism

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ARTICLE;

EID: 0042262416     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol007060u     Document Type: Article
Times cited : (17)

References (45)
  • 24
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    • (e) Yamazaki, T.; Hiraoka, S.; Kitazume, T. Tetrahedron: Asymmetry 1997, 8, 1157. For the intriguing cyclization of this compound in a 5-endo-trig manner, see: Yamazaki, T.; Hiraoka, S.; Sakamoto, J.; Kitazume, T. J. Phys. Chem. A 1999, 103, 6820.
    • (1997) Tetrahedron: Asymmetry , vol.8 , pp. 1157
    • Yamazaki, T.1    Hiraoka, S.2    Kitazume, T.3
  • 25
    • 0000340553 scopus 로고    scopus 로고
    • (e) Yamazaki, T.; Hiraoka, S.; Kitazume, T. Tetrahedron: Asymmetry 1997, 8, 1157. For the intriguing cyclization of this compound in a 5-endo-trig manner, see: Yamazaki, T.; Hiraoka, S.; Sakamoto, J.; Kitazume, T. J. Phys. Chem. A 1999, 103, 6820.
    • (1999) J. Phys. Chem. A , vol.103 , pp. 6820
    • Yamazaki, T.1    Hiraoka, S.2    Sakamoto, J.3    Kitazume, T.4
  • 26
    • 0013461581 scopus 로고
    • For other examples of nucleophilic S-O bond cleavage of sulfonates, see: (a) Baarschers, W. H. Can. J. Chem. 1976, 54, 3056.
    • (1976) Can. J. Chem. , vol.54 , pp. 3056
    • Baarschers, W.H.1
  • 28
    • 0001071115 scopus 로고
    • Trost, B. M., Ed.: Pergamon Press: New York
    • For other preparation methods of allylic alcohols, see: Kelly, S. E. In Comprehensive Organic Synthesis; Trost, B. M., Ed.: Pergamon Press: New York, 1991; Vol. 1, p 729.
    • (1991) Comprehensive Organic Synthesis , vol.1 , pp. 729
    • Kelly, S.E.1
  • 29
    • 0042407476 scopus 로고    scopus 로고
    • note
    • Because TMS ethers were not cleaved by the workup procedure, TBS protection was not required for 5g and h.
  • 32
    • 0041906242 scopus 로고    scopus 로고
    • note
    • A smaller amount of fluoride ion source significantly affected the conversion of 7e to 15e: 0.1 equiv of TBAF yielded only 32% of 15e with 56% recovery of 7e.
  • 33
    • 0041405128 scopus 로고    scopus 로고
    • note
    • 6 was used as the internal standard.
  • 40
    • 0003612579 scopus 로고
    • Isotope Effects in Chemical Reactions Van Nostrand Reinhold Co.: New York
    • 18O is reported to be at most 1.19. See: Collins, C. J.; Bowman, N. S. In Isotope Effects in Chemical Reactions (ACS Monograph 167); Van Nostrand Reinhold Co.: New York, 1970; p 16.
    • (1970) ACS Monograph , vol.167 , pp. 16
    • Collins, C.J.1    Bowman, N.S.2
  • 44
    • 0042908268 scopus 로고    scopus 로고
    • note
    • 2). After usual workup, the crude material was dissolved in MeOH where 4.0 equiv of NaOMe was added at 0 °C. Stirring at room temperature (0.5 h) and the usual workup and purification by silica gel column chromatography gave 21 (0.062 g, 0.352 mmol) in 95% yield.
  • 45
    • 0042407475 scopus 로고    scopus 로고
    • note
    • 2.


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