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Volumn 49, Issue 49, 2008, Pages 6991-6994

Stereospecific epoxide-opening reactions of 1,1-dibromo-3,4-epoxy-1-alkenes with carbon nucleophiles

Author keywords

1,1 Dibromo 3,4 epoxy 1 alkene; 3,4 Disubstituted lactone; Allyltributylstannane; Epoxide opening reaction; Ketene silyl acetal; Lewis acid

Indexed keywords

ALKENE; CARBON; EPOXIDE; GAMMA BUTYROLACTONE DERIVATIVE; KETENE DERIVATIVE; LEWIS ACID;

EID: 54049141203     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.09.115     Document Type: Article
Times cited : (9)

References (18)
  • 1
    • 54049125813 scopus 로고    scopus 로고
    • Klunder, J. M.; Posner, G. H. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991, Vol. 3, pp 207-239.
    • Klunder, J. M.; Posner, G. H. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991, Vol. 3, pp 207-239.
  • 2
    • 54049129335 scopus 로고    scopus 로고
    • Knight, D. W. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991, vol. 3, pp 241-270.
    • Knight, D. W. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991, vol. 3, pp 241-270.
  • 3
    • 54049083093 scopus 로고    scopus 로고
    • Garratt, P. J. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991, Vol. 3, pp 271-292.
    • Garratt, P. J. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991, Vol. 3, pp 271-292.
  • 7
    • 0000560517 scopus 로고
    • Epoxide-opening reactions by use of heteroatoms were reported, see:
    • Epoxide-opening reactions by use of heteroatoms were reported, see:. Nicolaou K.C., Prasad C.V.C., Somers P.K., and Hwang C.-K. J. Am. Chem. Soc. 111 (1989) 5330-5334
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 5330-5334
    • Nicolaou, K.C.1    Prasad, C.V.C.2    Somers, P.K.3    Hwang, C.-K.4
  • 15
    • 54049084649 scopus 로고    scopus 로고
    • When an excess amount of allyltributylstannane (5 equiv) was used in the allylation reaction, better diastereoselectivity (dr > 99:1) was observed.
    • When an excess amount of allyltributylstannane (5 equiv) was used in the allylation reaction, better diastereoselectivity (dr > 99:1) was observed.
  • 16
    • 4444296427 scopus 로고    scopus 로고
    • 4-mediated substitution reaction of epoxides with ketene silyl acetals leading to γ-butyrolactones has been reported, although the presence of halogen atoms at the vicinal positions of epoxides was indispensable for the conversion except for ethylene oxide, see:
    • 4-mediated substitution reaction of epoxides with ketene silyl acetals leading to γ-butyrolactones has been reported, although the presence of halogen atoms at the vicinal positions of epoxides was indispensable for the conversion except for ethylene oxide, see:. Maslak V., Matović R., and Saičić R.N. Tetrahedron 60 (2004) 8957-8966
    • (2004) Tetrahedron , vol.60 , pp. 8957-8966
    • Maslak, V.1    Matović, R.2    Saičić, R.N.3
  • 17
    • 0029402357 scopus 로고
    • Five equiv of ketene silyl acetal 3 were required for completion of the reaction, because 3 prepared by the Mikami protocol: consisted of an inseparable mixture of ketene silyl acetal and ethyl (2-trimethylsilyl)acetate as well as because of its high susceptibility to Lewis acids
    • Five equiv of ketene silyl acetal 3 were required for completion of the reaction, because 3 prepared by the Mikami protocol:. Mikami K., Matsumoto S., Ishida A., Takamuku S., Suenobu T., and Fukuzumi S. J. Am. Chem. Soc. 117 (1995) 11134-11141 consisted of an inseparable mixture of ketene silyl acetal and ethyl (2-trimethylsilyl)acetate as well as because of its high susceptibility to Lewis acids
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 11134-11141
    • Mikami, K.1    Matsumoto, S.2    Ishida, A.3    Takamuku, S.4    Suenobu, T.5    Fukuzumi, S.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.