
%0 Journal Article
%A Dancer, RJ 
%A Haynes, RK 
%A Loughlin, WA 
%A Vonwiller, SC 
%T Efficient Trapping of Ketone Enolates With Acrylate and &#946;-Sulfonylacrylate Thioesters, &#946;-Sulfonyl-, &#946;-Sulfinyl- and &#946;-Chloro-Vinyl Ketones; Facile Preparation of a Hydrindanone, <I>cis</I>-Dimethyloctalone, and Unsaturated 1,5-Dicarbonyl Compounds
%J Australian Journal of Chemistry
%D 1990/08/01
%V 43
%N 8
%P 1375-1389
%K 
%R https://doi.org/10.1071/CH9901375
%U https://www.publish.csiro.au/paper/CH9901375 
%X Tandem conjugate addition-ring closure involving reaction of the lithium enolate arising from conjugate addition of lithiated (E)-but-2- enyldiphenylphosphine oxide to 2-methyl-cyclopent-2-enone with two moles of t-butylthioacrylate generates a hydrindanol, and, in the presence of copper(I), a lactone derived from the hydrindanol. &#946;-Sulfonylacrylate phenyl and t-butyl thioesters, &#946;-chlorovinyl, &#946;- sulfonyl- and &#946;-sulfinyl-vinyl ketones react with the foregoing enolate, and with the enolate generated through conjugate addition of a methylcuprate to 2-methylcyclohexenone to give unsaturated 1,5-dicarbonyl compounds. The &#946;-chlorovinyl ketones in particular react rapidly and in high yield. 2-Methylcyclohexenone has thereby been converted into a cis-dimethyl octalone; the conversion illustrates the effectiveness of &#946;-chlorovinyl methyl ketone in the Robinson annelation. Reactions of the lithium enolate and titanium enol of 2,6- dimethylcyclohexanone with the &#946;-substituted enones to give the corresponding unsaturated 1,5-dicarbonyl compounds and other products are also recorded. 
