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Volumn 17, Issue SUPPL., 2005, Pages

Synthesis and CD spectroscopic study of chiral C2-symmetric (+)-2-oxaadamantane-4,8-dione

Author keywords

2 oxaadamantane 4,8 dione; Absolute configuration; CD spectroscopy; Enantiospecific synthesis; Molecular rearrangement

Indexed keywords

2 OXAADAMANTANE 4,8 DIONE; 2 OXATRICYCLO[3.3.1.1 3,7]DECANE 4,8 DIONE; 4 BROMO 3 METHOXY 2 OXATRICYCLO[4.3.1.0 3,8]DECAN 10 ONE; ADAMANTANE DERIVATIVE; SILVER NITRATE; UNCLASSIFIED DRUG;

EID: 21844472491     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.20118     Document Type: Conference Paper
Times cited : (7)

References (22)
  • 1
    • 0001447220 scopus 로고
    • Heteroadamantanes. 3. The effect of changing electron demand on O-3 participation in the solvolysis of 2-oxaadamantanes
    • (a) Subramaniam R, Fort Jr RC. Heteroadamantanes. 3. The effect of changing electron demand on O-3 participation in the solvolysis of 2-oxaadamantanes. J Org Chem 1984;49:2891-2896.
    • (1984) J Org Chem , vol.49 , pp. 2891-2896
    • Subramaniam, R.1    Fort Jr., R.C.2
  • 2
    • 21844463106 scopus 로고
    • Advances in heteroadamantane synthesis
    • (b) For an earlier review see: Averina NV, Zefirov NS. Advances in heteroadamantane synthesis. Usp Khim (Russ Chem Rev) 1976;45: 1077-1101.
    • (1976) Usp Khim (Russ Chem Rev) , vol.45 , pp. 1077-1101
    • Averina, N.V.1    Zefirov, N.S.2
  • 3
    • 21844441446 scopus 로고
    • Synthesis of 5,5′-bi-2-oxaadamantane
    • (a) Teager DS, Murray Jr RK. Synthesis of 5,5′-bi-2-oxaadamantane. J Org Chem 1993;58:5560-5561.
    • (1993) J Org Chem , vol.58 , pp. 5560-5561
    • Teager, D.S.1    Murray Jr., R.K.2
  • 4
    • 0000996590 scopus 로고
    • The replacement of the carbonyl group of adamantanone by an oxygen or sulfur atom and the one-step transformation of 2-methyladamantan-2-ol into 2-oxaadamantane; an efficient new synthesis of 2-oxa- and 2-thiaadamantane
    • (b) Suginome H, Yamada S. The replacement of the carbonyl group of adamantanone by an oxygen or sulfur atom and the one-step transformation of 2-methyladamantan-2-ol into 2-oxaadamantane; an efficient new synthesis of 2-oxa- and 2-thiaadamantane. Synthesis 1986:741-743.
    • (1986) Synthesis , pp. 741-743
    • Suginome, H.1    Yamada, S.2
  • 6
    • 0034733134 scopus 로고    scopus 로고
    • Observation of a stable carbocation in a consecutive Criegee rearrangement with trifluoroperacetic acid
    • (b) Krasutsky PA, Kolomitsyn IV, Kiprof P, Carlson RM, Fokin AA. Observation of a stable carbocation in a consecutive Criegee rearrangement with trifluoroperacetic acid. J Org Chem 2000;65:3926-3933.
    • (2000) J Org Chem , vol.65 , pp. 3926-3933
    • Krasutsky, P.A.1    Kolomitsyn, I.V.2    Kiprof, P.3    Carlson, R.M.4    Fokin, A.A.5
  • 9
    • 0035857253 scopus 로고    scopus 로고
    • Design, synthesis and cation-binding properties of novel adamantane- and 2-oxaadamantane-containing crown ethers
    • (a) Mlinaric-Majerski K, Kragol G. Design, synthesis and cation-binding properties of novel adamantane- and 2-oxaadamantane-containing crown ethers. Tetrahedron 2001;57:449-457.
    • (2001) Tetrahedron , vol.57 , pp. 449-457
    • Mlinaric-Majerski, K.1    Kragol, G.2
  • 10
    • 0031562444 scopus 로고    scopus 로고
    • Synthesis and alkali metal picrate extraction capabilities of novel cage-functionalized 17-crown-5 and 17-crown-6 ethers
    • (b) Marchand AP, Kumar KA, McKim AS. Synthesis and alkali metal picrate extraction capabilities of novel cage-functionalized 17-crown-5 and 17-crown-6 ethers. Tetrahedron 1997;53:3467-3474.
    • (1997) Tetrahedron , vol.53 , pp. 3467-3474
    • Marchand, A.P.1    Kumar, K.A.2    McKim, A.S.3
  • 13
    • 0035156746 scopus 로고    scopus 로고
    • Determination of the absolute configuration of bicyclo[3.3.1]nonane-2,7- dione by circular dichroism spectroscopy and chemical correlation
    • Butkus E, Stončius S, Žilinskas A. Determination of the absolute configuration of bicyclo[3.3.1]nonane-2,7-dione by circular dichroism spectroscopy and chemical correlation. Chirality 2001;13:694-698.
    • (2001) Chirality , vol.13 , pp. 694-698
    • Butkus, E.1    Stončius, S.2    Žilinskas, A.3
  • 14
    • 0006468334 scopus 로고    scopus 로고
    • Determination of absolute and relative configuration by chiroptical methods
    • Helmchen RW, Hoffmann RW, Mulzer J, Schaumann E, editors. Stuttgart: Thieme . Workbench edition, E21, and references cited therein
    • Gawronski J. Determination of absolute and relative configuration by chiroptical methods. In: Helmchen RW, Hoffmann RW, Mulzer J, Schaumann E, editors. Methods of organic chemistry (Houben-Weyl). Stuttgart: Thieme; 1996. Workbench edition, E21, vol 1, p 499-533 and references cited therein.
    • (1996) Methods of Organic Chemistry (Houben-Weyl) , vol.1
    • Gawronski, J.1
  • 15
    • 0006456570 scopus 로고
    • Sensitivity of circular dichroism of β-diketones to minute changes in the orientation of chromophores
    • Sumiyoshi M, Kuritani H, Shingu K, Nakagawa M. Sensitivity of circular dichroism of β-diketones to minute changes in the orientation of chromophores. Tetrahedron Lett 1980;21:1243-1246.
    • (1980) Tetrahedron Lett , vol.21 , pp. 1243-1246
    • Sumiyoshi, M.1    Kuritani, H.2    Shingu, K.3    Nakagawa, M.4
  • 16
    • 0001606659 scopus 로고
    • An Analysis of the circular dichroism spectra of bicyclo[3.3.1]nonane- diones
    • Berg U, Butkus E. An Analysis of the circular dichroism spectra of bicyclo[3.3.1]nonane-diones. J Chem Res (S) 1993:116-117.
    • (1993) J Chem Res (S) , pp. 116-117
    • Berg, U.1    Butkus, E.2
  • 19
    • 0030900927 scopus 로고    scopus 로고
    • Stereochemical studies of bicyclo[5.3.1]undecane-8,11-dione. Conformational analysis, enantiomer separation, CD-spectroscopy and enolization
    • (a) Berg U, Butkus E, Frejd T, Bromander S. Stereochemical studies of bicyclo[5.3.1]undecane-8,11-dione. Conformational analysis, enantiomer separation, CD-spectroscopy and enolization. Tetrahedron 1997;53:5339-5348.
    • (1997) Tetrahedron , vol.53 , pp. 5339-5348
    • Berg, U.1    Butkus, E.2    Frejd, T.3    Bromander, S.4
  • 21
    • 1642275595 scopus 로고    scopus 로고
    • Determination of absolute configuration using concerted ab initio DFT calculations of electronic circular dichroism and optical rotation: Bicyclo[3.3.1]nonane diones
    • (c) Stephens PJ, McCann DM, Butkus E, Stončius S, Cheeseman JR, Frisch MJ. Determination of absolute configuration using concerted ab initio DFT calculations of electronic circular dichroism and optical rotation: bicyclo[3.3.1]nonane diones. J Org Chem 2004;69:1948-1958.
    • (2004) J Org Chem , vol.69 , pp. 1948-1958
    • Stephens, P.J.1    McCann, D.M.2    Butkus, E.3    Stončius, S.4    Cheeseman, J.R.5    Frisch, M.J.6
  • 22
    • 0039738245 scopus 로고
    • Chiroptische eigenschaften von thiaadamantan-derivaten
    • Snatzke G, Wolfram B. Chiroptische Eigenschaften von Thiaadamantan- derivaten. Tetrahedron 1972;28:655-662.
    • (1972) Tetrahedron , vol.28 , pp. 655-662
    • Snatzke, G.1    Wolfram, B.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.