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Volumn 49, Issue 29-30, 2008, Pages 4470-4472

Chelation control in the [3+3] annulation reaction of alkoxy-substituted 1,1-diacylcyclopropanes with 1,3-bis(trimethylsilyloxy)-1,3-butadienes

Author keywords

Arenes; Cyclizations; Cyclopropanes; Regioselectivity; Silyl enol ethers

Indexed keywords

1,1 DIACYLCYCLOPROPANE DERIVATIVE; 1,3 BIS(TRIMETHYLSILYLOXY) 1,3 BUTADIENE DERIVATIVE; 1,3 BUTADIENE DERIVATIVE; PROPANE;

EID: 44749092501     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.05.066     Document Type: Article
Times cited : (7)

References (17)
  • 1
    • 0007047259 scopus 로고    scopus 로고
    • Steglich W., Fugmann B., and Lang-Fugmann S. (Eds), Thieme, Stuttgart
    • In: Steglich W., Fugmann B., and Lang-Fugmann S. (Eds). Römpp Lexikon Naturstoffe (1997), Thieme, Stuttgart
    • (1997) Römpp Lexikon Naturstoffe
  • 4
    • 33947178424 scopus 로고    scopus 로고
    • For a review of [3+3] cyclizations, see:
    • For a review of [3+3] cyclizations, see:. Feist H., and Langer P. Synthesis (2007) 327
    • (2007) Synthesis , pp. 327
    • Feist, H.1    Langer, P.2
  • 5
    • 0036200130 scopus 로고    scopus 로고
    • For a review of 1,3-bis(silyl enol ethers), see:
    • For a review of 1,3-bis(silyl enol ethers), see:. Langer P. Synthesis (2002) 441
    • (2002) Synthesis , pp. 441
    • Langer, P.1
  • 6
    • 0003441987 scopus 로고    scopus 로고
    • For reviews of chelation control in Lewis acid-mediated reactions, see:, Oxford University Press, Oxford
    • For reviews of chelation control in Lewis acid-mediated reactions, see:. Yamamoto H. Lewis Acid Chemistry (1999), Oxford University Press, Oxford
    • (1999) Lewis Acid Chemistry
    • Yamamoto, H.1
  • 10
    • 0000915551 scopus 로고    scopus 로고
    • Chelation control has been reported for the [4+3] annulation reaction of benzyloxy-substituted 1,4-dicarbonyl compounds with bis(silyl enol ethers):
    • Chelation control has been reported for the [4+3] annulation reaction of benzyloxy-substituted 1,4-dicarbonyl compounds with bis(silyl enol ethers):. Molander G.A., and Eastwood P.R. J. Org. Chem. 61 (1996) 1910
    • (1996) J. Org. Chem. , vol.61 , pp. 1910
    • Molander, G.A.1    Eastwood, P.R.2
  • 12
    • 44749089886 scopus 로고    scopus 로고
    • note
    • 3), 202.9, 203.6 (CO).
  • 15
    • 44749090895 scopus 로고    scopus 로고
    • note
    • 4 (272.72): C, 57.25; H, 6.28. Found: C, 57.24; H, 6.39. All new products gave correct spectroscopic data and elemental analyses and/or high resolution mass data.
  • 16
    • 0010250493 scopus 로고    scopus 로고
    • Reactions of acceptor-substituted cyclopropanes have been classified by Danishefsky in terms of 'strictly nucleophilic ring openings', 'electrophilically assisted ring openings', and 'spiro-activations': Danishefsky, S. J. Acc. Chem. Res. 1979, 66. In the domino '[3+3]-cyclization-homo-Michael' reaction reported herein two effects are operating: (a) a 'dynamic spiro-activation' and (b) activation by an electrophile. For a dynamic spiro activation, see: Zefirov, N. S.; Kozhushkov, S. I.; Kuznetsova, T. S. Tetrahedron 1982, 38, 1693.
    • Reactions of acceptor-substituted cyclopropanes have been classified by Danishefsky in terms of 'strictly nucleophilic ring openings', 'electrophilically assisted ring openings', and 'spiro-activations': Danishefsky, S. J. Acc. Chem. Res. 1979, 66. In the domino '[3+3]-cyclization-homo-Michael' reaction reported herein two effects are operating: (a) a 'dynamic spiro-activation' and (b) activation by an electrophile. For a dynamic spiro activation, see: Zefirov, N. S.; Kozhushkov, S. I.; Kuznetsova, T. S. Tetrahedron 1982, 38, 1693.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.