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Volumn 351, Issue 14-15, 2009, Pages 2310-2314

Palladium-Catalyzed isomerization of exo-methylenic allylic alcohols

Author keywords

Alkenes; Allylic alcohols; Hydrogenation; Isomerization; Palladium

Indexed keywords


EID: 70350610678     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200900309     Document Type: Article
Times cited : (3)

References (31)
  • 15
    • 0035965756 scopus 로고    scopus 로고
    • For previous reports of rhodium-catalyzed isomerizations of exo-methylenic cyclohexanes, exo-methylenic ketones and exo-methylenic lactones, : a
    • For previous reports of rhodium-catalyzed isomerizations of exo-methylenic cyclohexanes, exo-methylenic ketones and exo-methylenic lactones, see : a) P. Stahl, L. Kissau, R. Mazitschek, A. Huwe, P. Furet, A. Giannis, H. Waldmann, J. Am. Chem. Soc. 2001,123,11586-11593;
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 11586-11593
    • Stahl, P.1    Kissau, L.2    Mazitschek, R.3    Huwe, A.4    Furet, P.5    Giannis, A.6    Waldmann, H.7
  • 18
    • 70350599596 scopus 로고    scopus 로고
    • 2
    • 2.
  • 19
    • 70350610740 scopus 로고    scopus 로고
    • A mechanism involving a π-allyl palladium intermediate would be likely to incorporate either one or four equivalents of deuterium.
    • A mechanism involving a π-allyl palladium intermediate would be likely to incorporate either one or four equivalents of deuterium.
  • 22
    • 70350605571 scopus 로고    scopus 로고
    • Treatment of trisubstituted allylic alcohol 2 with 3 mol% Pd/C in IPA under a balloon of deuterium gas for eight hours resulted in 60% incorporation of deuterium into its vinylic position.
    • Treatment of trisubstituted allylic alcohol 2 with 3 mol% Pd/C in IPA under a balloon of deuterium gas for eight hours resulted in 60% incorporation of deuterium into its vinylic position.
  • 23
    • 70350608233 scopus 로고    scopus 로고
    • Experiments employing < 1 bar of hydrogen resulted in competing oxidation of allylic alcohol 6a to its corresponding ketone.
    • Experiments employing < 1 bar of hydrogen resulted in competing oxidation of allylic alcohol 6a to its corresponding ketone.
  • 24
    • 70350591930 scopus 로고    scopus 로고
    • All syn-/anti-hydrogenated alcohols 8/9 were formed in a ratio ranging from 1:1 to 2:1, with major isomers unassigned.
    • All syn-/anti-hydrogenated alcohols 8/9 were formed in a ratio ranging from 1:1 to 2:1, with major isomers unassigned.
  • 25
    • 0001408311 scopus 로고
    • Allylic alcohols 6a-d and 6g-j were prepared via amethylenation of the appropriate aldehyde with formaldehyde and dimethylamine hydrochloride, followed by addition of the corresponding Grignard reagent; a
    • Allylic alcohols 6a-d and 6g-j were prepared via amethylenation of the appropriate aldehyde with formaldehyde and dimethylamine hydrochloride, followed by addition of the corresponding Grignard reagent; see : a) C. S. Marvel, R. L. Myers, J. H. Saunders, J. Am. Chem. Soc. 1948, 70, 1694-1699;
    • (1948) J. Am. Chem. Soc. , vol.70 , pp. 1694-1699
    • Marvel, C.S.1    Myers, R.L.2    Saunders, J.H.3
  • 27
  • 28
    • 0038606694 scopus 로고    scopus 로고
    • Allylic alcohols 6e, f were prepared via addition of the appropriate pyridyl-Grignard reagent to 2-ethylacrolein
    • Allylic alcohols 6e, f were prepared via addition of the appropriate pyridyl-Grignard reagent to 2-ethylacrolein; see: F. Trécourt, G. Breton, V. Bonnet, F. Mongin, F. Marsais, G. Quéguiner, Tetrahedron 2000, 56, 1349-1360.
    • (2000) Tetrahedron , vol.56 , pp. 1349-1360
    • Trécourt, F.1    Breton, G.2    Bonnet, V.3    Mongin, F.4    Marsais, F.5    Quéguiner, G.6
  • 30
    • 70350613306 scopus 로고    scopus 로고
    • 1H NMR Spectra Than the Alkene Protons of Their Corresponding (Z)-isomers
    • 1H NMR spectra than the alkene protons of their corresponding (Z)-isomers.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.