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Volumn 348, Issue 15, 2006, Pages 2133-2147

Cyclopropyl building blocks for organic synthesis, 131. Palladium-catalyzed bicyclization with carbonyl insertion of alkenyl-tethered propargyl carbonates towards a scalable synthesis of various 2-(bicyclo[3.1.0]hex-1-yl)acrylates

Author keywords

Bicyclic vinylcyclopropanes; Carbonylations; Cycloisomerizations; Homogeneous catalysis; Palladium catalysts; Ring strain

Indexed keywords


EID: 33750524264     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200606155     Document Type: Article
Times cited : (17)

References (36)
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    • note
    • The target 2-(bicyclo[3.1.0]hex-1-yl)acrylates produced for an ultimate use in low-shrinkage dental composites, must remain colorless even after extended exposure to air and light. They also should have minimal biological activity, e.g. cytotoxity.
  • 15
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    • The original protocol was modified (see Experimental Section)
    • W. J. Bailey, E. Fujiwara, J. Am. Chem. Soc. 1955, 77, 165-166. The original protocol was modified (see Experimental Section).
    • (1955) J. Am. Chem. Soc. , vol.77 , pp. 165-166
    • Bailey, W.J.1    Fujiwara, E.2
  • 17
    • 33750523256 scopus 로고    scopus 로고
    • note
    • With this modification even less C-H acidic α-acetylamides can be alkylated.
  • 19
    • 0000049821 scopus 로고
    • Palladium acetate has been applied as a precatalyst for carbonylative transformations of propargyl carbonates. J. Tsuji, T. Mandai, Angew. Chem. 1995, 107, 2830-2854;
    • (1995) Angew. Chem. , vol.107 , pp. 2830-2854
    • Tsuji, J.1    Mandai, T.2
  • 21
    • 33750519677 scopus 로고    scopus 로고
    • note
    • 2 is essential. All attempts to perform the bicyclization either under ligand-free conditions, or in the presence of less ligand either failed completely or led to immediate formation of palladium black.
  • 22
    • 0034249671 scopus 로고    scopus 로고
    • Trialkyl phosphites are known to be able to reduce palladium(II) to palladium(0), see: I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009-3066.
    • (2000) Chem. Rev. , vol.100 , pp. 3009-3066
    • Beletskaya, I.P.1    Cheprakov, A.V.2
  • 23
    • 0034127063 scopus 로고    scopus 로고
    • The favorable role of the quaternary ammonium halide most probably is to provide an appropriate concentration of halide ions which help to stabilize the palladium(0) species, see: C. Amatore, A. Jutand, Acc. Chem. Res. 2000, 33, 314-321.
    • (2000) Acc. Chem. Res. , vol.33 , pp. 314-321
    • Amatore, C.1    Jutand, A.2
  • 24
    • 33750496625 scopus 로고    scopus 로고
    • note
    • It is noteworthy, that the use of a tetraalkylammonium iodide causes immediate formation of palladium black.
  • 25
    • 20044390256 scopus 로고    scopus 로고
    • For the influence of gem-disubstitution on the success of cyclization reactions see the review: M. E. Jung, G. Piizzi, Chem. Rev. 2005, 105, 1735-1766.
    • (2005) Chem. Rev. , vol.105 , pp. 1735-1766
    • Jung, M.E.1    Piizzi, G.2
  • 29
    • 33750523649 scopus 로고    scopus 로고
    • Dissertation, Universität Göttingen, p. 145
    • V. Bagutski, Dissertation, Universität Göttingen, 2004, p. 145.
    • (2004)
    • Bagutski, V.1
  • 30
    • 33750495396 scopus 로고    scopus 로고
    • note
    • An attempted bicyclization of 7g in glacial acetic acid gave only a trace amount (ca. 5%) of the corresponding bicyclic acrylic acid.
  • 36
    • 33750511556 scopus 로고    scopus 로고
    • Dissertation, Universität Göttingen, p. 77
    • This procedure is also viable for the hydrolysis of ethyl acrylates to give the corresponding acids in excellent yields: V. Bagutski, Dissertation, Universität Göttingen, 2004, p. 77.
    • (2004)
    • Bagutski, V.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.