Stereoselective addition of alcohol to acetylenecarboxylate catalyzed by silver(I) salt

Chemistry Letters

Volumn , Issue 9, 1996, Pages 727-728

  Kataoka, Yasutaka ^a   Matsumoto, Osamu ^a   Tani, Kazuhide ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0030351646     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1996.727     Document Type: Article

References (19)

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19. In the reaction of DMAD with MeOH, an acetal product prepared from the second addition of MeOH to the vinyl ether 1 was not obtained at all, even if a prolonged reaction time was employed. When propan-1,3-diol was used as an alcohol, DMAD gave only the corresponding γ-hydroxypropyl vinyl ether, but ethyl 2-tridecynoate (6) formed a mixture of the corresponding cyclic acetal and ketone. The reason why the second addition of alcohol to vinyl ether 7 occurred smoothly is not clear at present.