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Volumn 40, Issue 5, 1999, Pages 871-874

Copper (I) mediated highly diastereoselective conjugate addition of Grignard reagents to functionalised 6-membered ring cycloalkenols. Synthesis of cyclohexanes derivatives substituted on three contiguous atoms

Author keywords

2 Hydroxycyclohexane carboxylates; 2 Silyloxycyclohexene carboxylates; Conjugate Addition; Copper catalysed Grignard reactions; Diastereoselectivity; Ketene acetals; Michael reactions

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; COPPER ION; CYCLOHEXANE DERIVATIVE; REAGENT;

EID: 0033613771     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02543-X     Document Type: Article
Times cited : (9)

References (19)
  • 1
    • 84909451416 scopus 로고
    • For papers of related interest see : (a) J. F. Normant, Synthesis, 1972, 63-80.
    • (1972) Synthesis , pp. 63-80
    • Normant, J.F.1
  • 4
    • 0004583389 scopus 로고
    • B. M. Trost, I. Fleming, Eds., Pergamon Press (Oxford), Chapter 1.4
    • (d) J. A. Kozlowski In "Comprehensive Organic Synthesis", B. M. Trost, I. Fleming, Eds., Pergamon Press (Oxford), 1991, Vol. 4, Chapter 1.4.
    • (1991) Comprehensive Organic Synthesis , vol.4
    • Kozlowski, J.A.1
  • 12
    • 10544248277 scopus 로고
    • Concerning the use of TMS Halide in conjugate addition reactions see for instance (a) E. J. Corey, N. W. Boaz, Tetrahedron Lett., 1985, 26, 6019-6022.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 6019-6022
    • Corey, E.J.1    Boaz, N.W.2
  • 15
    • 0013531401 scopus 로고    scopus 로고
    • 3 and extraction with diethyl ether finally furnished β-silyloxy ester. The last deprotection step was accomplished according to known procedures (see 9 and 10)
    • 3 and extraction with diethyl ether finally furnished β-silyloxy ester. The last deprotection step was accomplished according to known procedures (see 9 and 10).
  • 18
    • 0013489552 scopus 로고    scopus 로고
    • The diol 6e was obtained after treatment with 2N aqueous HCl in aceton for 2 hours at R. T. Removal of the dioxolane moiety was performed with potassium periodate at reflux of a mixture of dioxane and 0.1 N aqueous HCl. The same subsequent treatment as for 6e finally afforded 6f
    • The diol 6e was obtained after treatment with 2N aqueous HCl in aceton for 2 hours at R. T. Removal of the dioxolane moiety was performed with potassium periodate at reflux of a mixture of dioxane and 0.1 N aqueous HCl. The same subsequent treatment as for 6e finally afforded 6f.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.