
TY  - JOUR
A1  - Dancer, RJ 
A1  - Haynes, RK 
A1  - Loughlin, WA 
A1  - Vonwiller, SC 
T1  - 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
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1990
VL  - 43
IS  - 8
SP  - 1375
EP  - 1389
KW  - 
UR  - https://doi.org/10.1071/CH9901375 
N2  - 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. 
ER  -

