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Volumn 2012, Issue 2, 2012, Pages 74-84

Organozinc-promoted ring opening of cyclopropanols

Author keywords

Cyclopropanol; Homoenolate; Organozinc; Ring opening

Indexed keywords


EID: 84884183837     PISSN: 1551-7012     EISSN: 15517004     Source Type: Journal    
DOI: 10.3998/ark.5550190.0013.208     Document Type: Article
Times cited : (5)

References (52)
  • 12
    • 0242605792 scopus 로고    scopus 로고
    • de Meijere, A., Ed.; Thieme: Stuttgart, Chapter 2.1.2
    • (c) Ryu, I.; Murai, S. In Houben-Weyl Methods of Organic Chemistry; de Meijere, A., Ed.; Thieme: Stuttgart, 1997 ; Vol. E17c, Chapter 2.1.2, pp 1985- 2040.
    • (1997) Houben-Weyl Methods of Organic Chemistry , vol.E17C , pp. 1985-2040
    • Ryu, I.1    Murai, S.2
  • 17
    • 0000553317 scopus 로고
    • Zinc iodide-mediated isomerization of siloxycyclopropanes was known, but limited to bicyclo[n.1.0] compounds under 2 M concentrations: (a)
    • Zinc iodide-mediated isomerization of siloxycyclopropanes was known, but limited to bicyclo[n.1.0] compounds under 2 M concentrations: (a) Murai, S.; Aya, T.; Renge, T.; Ryu, I.; Sonoda, N. J. Org. Chem. 1974, 39, 858.
    • (1974) J. Org. Chem. , vol.39 , pp. 858
    • Murai, S.1    Aya, T.2    Renge, T.3    Ryu, I.4    Sonoda, N.5
  • 40
    • 29144530838 scopus 로고    scopus 로고
    • For a review of these preparations, see: (g)
    • For a review of these preparations, see: (g) Knochel, P. Sci Synthesis 2004, 3, 5.
    • (2004) Sci Synthesis , vol.3 , pp. 5
    • Knochel, P.1
  • 41
    • 0000710282 scopus 로고
    • Although the "Simmons-Smith" reagents are represented as one species for convenience, Schlenk equilibria are possible: (a)
    • Although the "Simmons-Smith" reagents are represented as one species for convenience, Schlenk equilibria are possible: (a) Denmark, S. E.; Edwards, J. P.; Wilson, S. R. J. Am. Chem. Soc. 1992, 114, 2592.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 2592
    • Denmark, S.E.1    Edwards, J.P.2    Wilson, S.R.3
  • 42
    • 84884174305 scopus 로고    scopus 로고
    • ref 12f
    • (b) ref 12f.
  • 44
    • 84884199484 scopus 로고    scopus 로고
    • note
    • 4Cl, the starting cyclopropanol was recovered cleanly with no formation of 2. This control experiment precludes mild acid-promoted ring opening of zinc cyclopropoxides.
  • 45
    • 78649324181 scopus 로고    scopus 로고
    • For a compilation of other methods, see: and references cited therein
    • For a compilation of other methods, see: Ziegler, D. T.; Steffens, A. M.; Funk, T. W. Tetrahedron Lett. 2010, 51, 6726 and references cited therein.
    • (2010) Tetrahedron Lett. , vol.51 , pp. 6726
    • Ziegler, D.T.1    Steffens, A.M.2    Funk, T.W.3
  • 46
    • 79955595133 scopus 로고    scopus 로고
    • A stereoselective synthesis of trans -2-substituted cyclopropanols was recently reported by taking advantage of equilibration of the cyclopropoxide intermediates
    • A stereoselective synthesis of trans -2-substituted cyclopropanols was recently reported by taking advantage of equilibration of the cyclopropoxide intermediates: Cheng, K.; Carroll, P. J.; Walsh, P. J. Org. Lett. 2011, 13, 2346.
    • (2011) Org. Lett. , vol.13 , pp. 2346
    • Cheng, K.1    Carroll, P.J.2    Walsh, P.J.3
  • 51
    • 84884176987 scopus 로고    scopus 로고
    • note
    • 13C NMR spectra did not indicate the presence of a deuterium in the resulting product 8.
  • 52
    • 84884188180 scopus 로고    scopus 로고
    • We successfully trapped zinc homoenolate B with CuCN•2LiCl for subsequent elaboration: Unpublished results
    • We successfully trapped zinc homoenolate B with CuCN•2LiCl for subsequent elaboration: Das, P. P.; Cha, J. K. Unpublished results.
    • Das, P.P.1    Cha, J.K.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.