Carbocyclic Ring Formation by the Intramolecular Reaction between Enol Silyl Ether and Allylic Acetate Moieties
作者： Akira Itoh , Koichiro Oshima , Hisashi Yamamoto , Hitosi Nozaki
DOI: 10.1246/BCSJ.53.2050
关键词:
摘要: The title reaction of trans-3-acetoxy-4-(4-methyl-3-trimethylsiloxy-3-pentenyl)cyclohexene proceeds in the presence Et2AlOAr, where Ar=2,6-di-t-butyl-4-methylphenyl, affording stereospecifically cis isomer 2,2-dimethylbicyclo[4.4.0]dec-9-en-3-one. In contrast, cis-disubstituted cyclohexene compound reacts only sluggishly to produce a mixture cis- and trans-fused octalones. Similar stereospecific effect allylic double bond configuration on ease cyclization has been observed synthesis karahanaenone from 3,7-dimethyl-6-trimethylsiloxy-2,6-octadienyl acetate related reactions.
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