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Volumn , Issue 22, 2008, Pages 2559-2561

Oxidative radical cyclisations for the synthesis of γ-lactones

Author keywords

[No Author keywords available]

Indexed keywords

COPPER DERIVATIVE; GAMMA LACTONE DERIVATIVE; MALONIC ACID DERIVATIVE; MANGANESE DERIVATIVE;

EID: 44349189891     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b802473a     Document Type: Article
Times cited : (37)

References (30)
  • 7
    • 0003544583 scopus 로고    scopus 로고
    • I. Ojima, Wiley-VCH, Weinheim, pp. 801-856
    • Catalytic Asymmetric Synthesis, ed., I. Ojima,, Wiley-VCH, Weinheim, 2000, pp. 801-856
    • (2000) Catalytic Asymmetric Synthesis, Ed.
  • 14
    • 0036354971 scopus 로고    scopus 로고
    • For oxidative radical synthesis of cyclopentanes using the ferrocenium cation see:
    • A. Studer S. Amrein Synthesis 2002 835
    • (2002) Synthesis , pp. 835
    • Studer, A.1    Amrein, S.2
  • 21
    • 0001618833 scopus 로고
    • Snider and McCarthy studied the oxidative radical cyclisation of dimethyl 4-pentenylmalonate 1 in a variety of solvents: see ref. 12 The oxidative cyclisation of dimethyl 4-pentenylmalonate 1 mediated by cerium(iv) ammonium nitrate has been studied. The use of copper(ii) nitrate as additive in AcOH gives the γ-lactone 2 in 74% yield, see:
    • B. B. Snider B. A. McCarthy J. Org. Chem. 1993 58 6217
    • (1993) J. Org. Chem. , vol.58 , pp. 6217
    • Snider, B.B.1    McCarthy, B.A.2
  • 23
    • 33646590682 scopus 로고
    • J. K. Kochi, Wiley, New York, pp. 594-623), we have reported that the combination of manganese(iii) acetate and copper(ii) triflate allows the formation of tethered bicyclic γ-lactones in excellent yields from dimethyl malonates containing a pendent carboxylic acid:
    • J. K. Kochi, in Free Radicals, ed., J. K. Kochi,, Wiley, New York, 1973, vol. 1, pp. 594-623
    • (1973) Free Radicals, Ed.
    • Kochi In, J.K.1
  • 24
    • 26944498973 scopus 로고    scopus 로고
    • For other references concerning the use of copper(ii) triflate in conjunction with manganese(iii) acetate see:
    • D. G. Hulcoop J. W. Burton Chem. Commun. 2005 4687
    • (2005) Chem. Commun. , pp. 4687
    • Hulcoop, D.G.1    Burton, J.W.2
  • 26
    • 2342505765 scopus 로고    scopus 로고
    • 1H NMR NOE experiments The stereochemical outcome of these reactions is in accord with the Beckwith-Houk model for the 5-exo-trig cyclisation of 5-hexenyl radicals see:
    • D. G. Hulcoop H. M. Sheldrake J. W. Burton Org. Biomol. Chem. 2004 2 965
    • (2004) Org. Biomol. Chem. , vol.2 , pp. 965
    • Hulcoop, D.G.1    Sheldrake, H.M.2    Burton, J.W.3
  • 29
    • 33845282341 scopus 로고
    • 2 in MeCN gives the lactone 6 and the methylenecyclopentane 14 in a 1.5: 1 ratio, whereas the methylenecyclopentane 14 is the sole product in DMSO. These results are in accord with Snider and McCarthy's study (ref. 12) For an example of the use of malonic hemi acids in manganese(iii) mediated reactions see:
    • D. C. Spellmeyer K. N. Houk J. Org. Chem. 1987 52 959
    • (1987) J. Org. Chem. , vol.52 , pp. 959
    • Spellmeyer, D.C.1    Houk, K.N.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.