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Volumn 131, Issue 7, 2009, Pages 2496-2498

Development of a formal [4+1] cycloaddition: Pd(OAc) 2-catalyzed intramolecular cyclopropanation of 1,3-dienyl β-keto esters and MgI 2-promoted vinylcyclopropane-Cyclopentene rearrangement

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTENE; CYCLOPROPANATION; INTRAMOLECULAR CYCLOPROPANATION; KETO ESTER; SUBSTITUTION PATTERNS; TAUTOMERIZATION; TWO-STEP PROCESS; VINYLCYCLOPROPANE;

EID: 67849114630     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja809226x     Document Type: Article
Times cited : (77)

References (57)
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    • (e) Wender, P. A.; Tebbe, M. J. Synthesis 1991, 1089. Pd:
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    • 34548173261 scopus 로고    scopus 로고
    • For reviews, see:a
    • For reviews, see:(a) Tanaka, K. Synlett 2007, 1977.
    • (2007) Synlett , pp. 1977
    • Tanaka, K.1
  • 18
    • 84982063874 scopus 로고    scopus 로고
    • Examples of [4 + 1] cycloadditions: (a) Lilienblum, W.; Hoffman, R. W. Chem. Ber. 1977, 110, 3405.
    • Examples of [4 + 1] cycloadditions: (a) Lilienblum, W.; Hoffman, R. W. Chem. Ber. 1977, 110, 3405.
  • 37
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    • Pei, T.; Wang, X.; Widenhoefer, R. A. J. Am. Chem. Soc. 2003, 125, 648 See also ref 9.
    • (b) Pei, T.; Wang, X.; Widenhoefer, R. A. J. Am. Chem. Soc. 2003, 125, 648 See also ref 9.
  • 44
    • 0026496883 scopus 로고    scopus 로고
    • Andersson and Backvall have reported hetero [4+1] reactions using Pd(II) catalysis. Andersson, P.; Bäckvall, J.-E. J. Am. Chem. Soc. 1992, 114, 8696.
    • Andersson and Backvall have reported hetero [4+1] reactions using Pd(II) catalysis. Andersson, P.; Bäckvall, J.-E. J. Am. Chem. Soc. 1992, 114, 8696.
  • 46
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    • 2 in related chemistry. (a) Yang, D.; Gao, Q.; Lee, C.-S.; Cheung, K.-K Org. Lett. 2002, 4, 3271.
    • 2 in related chemistry. (a) Yang, D.; Gao, Q.; Lee, C.-S.; Cheung, K.-K Org. Lett. 2002, 4, 3271.
  • 49
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    • 2 was less efficient.
    • 2 was less efficient.
  • 50
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    • 2, no product was observed.
    • 2, no product was observed.
  • 54
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    • This method was also ineffective with our substrates. For a VCP-CP rearrangement involving LiI, see
    • For a VCP-CP rearrangement involving LiI, see: Hashimoto, S.-i.; Shinoda, T.; Ikegami, S Tetrahedron Lett. 1986, 27, 2885. This method was also ineffective with our substrates.
    • (1986) Tetrahedron Lett , vol.27 , pp. 2885
    • Hashimoto, S.-I.1    Shinoda, T.2    Ikegami, S.3
  • 55
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    • Carreira and co-workers have utilized MgI2 for the ring opening of cyclopropyl carbonyls. (a) Alper, P. B.; Meyers, C.; Siegel, D. R.; Carreira, E. M. Angew. Chem., Int. Ed. 1999, 38, 3186.
    • Carreira and co-workers have utilized MgI2 for the ring opening of cyclopropyl carbonyls. (a) Alper, P. B.; Meyers, C.; Siegel, D. R.; Carreira, E. M. Angew. Chem., Int. Ed. 1999, 38, 3186.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.