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Volumn 63, Issue 42, 2007, Pages 10528-10533

Diol desymmetrization as an approach to the synthesis of unsymmetrical dienyl diesters

Author keywords

, Unsaturated hydroxy esters; Diol desymmetrization; Manganese dioxide; Tandem oxidation olefination

Indexed keywords

DIENYL DIESTER DERIVATIVE; ESTER DERIVATIVE; LACTONE DERIVATIVE; MANGANESE DIOXIDE; UNCLASSIFIED DRUG;

EID: 34548335298     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.07.089     Document Type: Article
Times cited : (27)

References (66)
  • 21
    • 0032575183 scopus 로고    scopus 로고
    • For examples of tandem reaction sequences of unsaturated diols using manganese dioxide as oxidant, see:
    • For examples of tandem reaction sequences of unsaturated diols using manganese dioxide as oxidant, see:. Wei X., and Taylor R.J.K. Tetrahedron Lett. 39 (1998) 3815-3818
    • (1998) Tetrahedron Lett. , vol.39 , pp. 3815-3818
    • Wei, X.1    Taylor, R.J.K.2
  • 22
  • 24
    • 34548347863 scopus 로고    scopus 로고
    • Taylor, R. J. K. Personal communication.
  • 30
    • 4444287266 scopus 로고    scopus 로고
    • A selective mono-oxidation of two identical primary alcohol functions using manganese dioxide has been reported;
    • A selective mono-oxidation of two identical primary alcohol functions using manganese dioxide has been reported;. Ziessel R., Nguyen P., Douce L., Cesario M., and Estournes C. Org. Lett. 6 (2004) 2865-2867
    • (2004) Org. Lett. , vol.6 , pp. 2865-2867
    • Ziessel, R.1    Nguyen, P.2    Douce, L.3    Cesario, M.4    Estournes, C.5
  • 31
    • 34548340423 scopus 로고    scopus 로고
    • The oxidizing capacity of manganese dioxide is also moderated by choice of solvent. Protic solvents, such as alcohols, are absorbed onto the surface of manganese dioxide and have a strong deactivating effect;
  • 34
    • 0000928373 scopus 로고
    • For the Wittig reaction of 2-hydroxytetrahydrofuran to give the corresponding α,β-unsaturated hydroxy product, see:
    • For the Wittig reaction of 2-hydroxytetrahydrofuran to give the corresponding α,β-unsaturated hydroxy product, see:. Denmark S.E., and Senanayake C.B.W. J. Org. Chem. 58 (1993) 1853-1858
    • (1993) J. Org. Chem. , vol.58 , pp. 1853-1858
    • Denmark, S.E.1    Senanayake, C.B.W.2
  • 45
    • 34548371515 scopus 로고    scopus 로고
    • Phillips, D. J.; Ridout, B. J.; Graham, A. E. Unpublished results.
  • 66
    • 34548347855 scopus 로고    scopus 로고
    • note
    • No products derived from the tandem oxidation/Wittig olefination were observed in the reaction of silica supported PCC (4 equiv), imidazole (4 equiv), and butanediol over the course of 24 h.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.