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Volumn 16, Issue 9, 2010, Pages 2696-2699

Diversity of products in the gold-catalyzed cyclization of 1-epoxy-1-alkynylcyclopropanes by using 1-oxyallyl cations

Author keywords

Alkynes; Cycloaddition; Epoxides; Gold; Oxycyclization

Indexed keywords

ALKYNES; DIASTEREO-SELECTIVITY; STEREO-SELECTIVE;

EID: 77149156607     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200903419     Document Type: Article
Times cited : (28)

References (68)
  • 9
    • 69049113944 scopus 로고    scopus 로고
    • For gold-catalyzed intermolecular cycloaddition reactions, see: a
    • For gold-catalyzed intermolecular cycloaddition reactions, see: a) N. D. Shapiro; Y. Shi, F. D. Toste, J. Am. Chem. Soc. 2009, 131, 11654;
    • (2009) J. Am. Chem. Soc , vol.131 , pp. 11654
    • Shapiro, N.D.1    Shi, Y.2    Toste, F.D.3
  • 23
  • 28
    • 0000456845 scopus 로고    scopus 로고
    • Cycloaddition of 1-oxyallyl cations is only operable with dienes, see a P. G. Gassman, D. A. Singleton, J. Org. Chem. 1986, 51, 3075;
    • Cycloaddition of 1-oxyallyl cations is only operable with dienes, see a) P. G. Gassman, D. A. Singleton, J. Org. Chem. 1986, 51, 3075;
  • 45
    • 77149159537 scopus 로고    scopus 로고
    • Screening of catalyst activity for this transformation is provided in the Supporting Information
    • Screening of catalyst activity for this transformation is provided in the Supporting Information.
  • 46
    • 77149160688 scopus 로고    scopus 로고
    • 1H NOE spectra of key compounds are provided in the Supporting Information.
    • 1H NOE spectra of key compounds are provided in the Supporting Information.
  • 47
    • 34249056927 scopus 로고    scopus 로고
    • For metal-catalyzed intramolecular cycloaddition of allenes, see: a
    • For metal-catalyzed intramolecular cycloaddition of allenes, see: a) X. Huang, L. Zhang, J. Am. Chem. Soc. 2007, 129, 6398;
    • (2007) J. Am. Chem. Soc , vol.129 , pp. 6398
    • Huang, X.1    Zhang, L.2
  • 65
    • 77149134090 scopus 로고    scopus 로고
    • When the strong nucleophile ROH replaced water in this catalysis, we observed diminished d.r. ratios of the resulting products 7a and 7e and their isomers 7a′ and 7e′. We note that the good d.r. value (d.r.> 20:1) was obtained for 7b/7b′ (R=Ph) because the cis-npentyl group of epoxide 1b impedes an external attack of the bulky phenol at the epoxy functionality. This side reaction is pronounced for small MeOH, giving 7a and 7a′ with a low d.r. value, Chemical Presented
    • When the strong nucleophile ROH replaced water in this catalysis, we observed diminished d.r. ratios of the resulting products 7a and 7e and their isomers 7a′ and 7e′. We note that the good d.r. value (d.r.> 20:1) was obtained for 7b/7b′ (R=Ph) because the cis-npentyl group of epoxide 1b impedes an external attack of the bulky phenol at the epoxy functionality. This side reaction is pronounced for small MeOH, giving 7a and 7a′ with a low d.r. value. (Chemical Presented)
  • 66
    • 77149125651 scopus 로고    scopus 로고
    • Preparation of chiral epoxide 4 is described in the Supporting Information.
    • Preparation of chiral epoxide 4 is described in the Supporting Information.
  • 67
    • 70450190983 scopus 로고    scopus 로고
    • Intermolecular [3+2] cycloaddition of an allene with an enol ether was reported with a platinum catalyst very recently, see H. Kusama, M. Ebisawa, H. Funami, N. Iwasawa, J. Am. Chem. Soc. 2009, 131, 16352.
    • Intermolecular [3+2] cycloaddition of an allene with an enol ether was reported with a platinum catalyst very recently, see H. Kusama, M. Ebisawa, H. Funami, N. Iwasawa, J. Am. Chem. Soc. 2009, 131, 16352.
  • 68
    • 77149172331 scopus 로고    scopus 로고
    • Catalyst screening for the cycloaddition of alcohol 2b with a diene is provided in the Supporting Information. The lower efficiency of the Brønsted acid is not surprising because cycloadducts 5a and 6a are sensitive to free protons.
    • Catalyst screening for the cycloaddition of alcohol 2b with a diene is provided in the Supporting Information. The lower efficiency of the Brønsted acid is not surprising because cycloadducts 5a and 6a are sensitive to free protons.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.